- Nitrogen-Doped Carbon-Incarcerated Zinc Electrodes as Heterogeneous Catalysts for Electrochemical Allylation of Carbonyl Compounds
-
Electrochemical allylation reactions of carbonyl compounds using cathodes prepared from nitrogen-doped carbon (NDC)-incarcerated zinc catalysts have been developed. A range of aldehydes and ketones afforded the desired allylic alcohols in high yields with 10 mol % zinc leaching, and the heterogeneous nature of the active species was suggested. Compared with bulk zinc electrodes, NDC-stabilized zinc nanoparticle species were compatible with a broader range of heteroaromatic substrates and enabled the use of an undivided cell.
- Masuda, Ryusuke,Yasukawa, Tomohiro,Yamashita, Yasuhiro,Kobayashi, Shū
-
p. 3453 - 3460
(2022/02/23)
-
- Amino alcohols using the optically active amino alcohol derivative bi- Nord complex boron - -
-
Disclosed are an amino alcohol-boron-binol complex as an intermediate, including Complex 3-1-1 shown below, and a method for preparing an optically active amino alcohol by using the same, wherein a racemic amino alcohol is resolved in an enationselective manner using a boron compound and a (R)- or (S)-binol, whereby an amino alcohol derivative with high optical purity can be prepared at high yield.
- -
-
Paragraph 0064; 0071-0076; 0223-0225; 0227-0231
(2021/04/16)
-
- Copper-Impregnated Magnesium-Lanthanum Mixed Oxide: A Reusable Heterogeneous Catalyst for Allylation of Aldehydes and Ketones
-
Copper-impregnated magnesium-lanthanum mixed oxide [Cu(II)/Mg?La] was used as catalyst in synthesis of homoallylic alcohols from aldehydes and ketones using allyltributylstannane as the allylating source. The present protocol provides a great application
- Laha, Soumi,Likhar, Pravin R.,Pogula, Jaya,Sreedhar, B.
-
supporting information
(2020/02/11)
-
- Palladacycles having normal and spiro chelate rings designed from bi- and tridentate ligands with an indole core: Structure, synthesis and applications as catalysts
-
1-Pyridin-2-ylmethyl-1H-indole-3-carbaldehyde and 1-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)-1H-indole-3-carbaldehyde were synthesized. Their condensation with benzyl amine resulted in indole core containing Schiff bases benzyl-(1-pyridin-2-ylmethyl-1H-in
- Singh, Mahabir P.,Saleem, Fariha,Pal, Ram S.,Singh, Ajai K.
-
p. 11342 - 11352
(2017/10/05)
-
- Asymmetric Allylation of Carbonyl Compounds Catalyzed by a Chiral Phosphine–Silver Complex
-
A catalytic, asymmetric allylation reaction of aldehydes or ketones with allyltrimethoxysilane was achieved by using a BINAP·AgBF4 [BINAP = 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl] complex as the chiral precatalyst and triethylamine as the
- Yanagisawa, Akira,Yang, Nan,Bamba, Kentaro
-
supporting information
p. 6614 - 6618
(2017/12/15)
-
- Palladacycles of unsymmetrical (N,C-,E) (E = S/Se) pincers based on indole: Their synthesis, structure and application in the catalysis of Heck coupling and allylation of aldehydes
-
Unsymmetrical (N,C,E)-type pincer ligand precursors [L1 and L2: E = S/Se] with an indole core were synthesized for the first time by the condensation of 1-(2-phenylsulfanyl/selenylethyl)-1H-indole-3-carbaldehyde with benzyl amine. The synthetic protocols
- Singh, Mahabir P.,Saleem, Fariha,Rao, Gyandshwar K.,Kumar,Joshi, Hemant,Singh, Ajai K.
-
p. 6718 - 6725
(2016/05/09)
-
- Chemoselective palladium-catalyzed deprotonative arylation/[1,2]-Wittig rearrangement of pyridylmethyl ethers
-
Control of chemoselectivity is one of the most challenging problems facing chemists and is particularly important in the synthesis of bioactive compounds and medications. Herein, the first highly chemoselective tandem C(sp3)-H arylation/[1,2]-Wittig rearrangement of pyridylmethyl ethers is presented. The efficient and operationally simple protocols enable generation of either arylation products or tandem arylation/[1,2]-Wittig rearrangement products with remarkable selectivity and good to excellent yields (60-99%). Choice of base, solvent, and reaction temperature play a pivotal role in tuning the reactivity of intermediates and controlling the relative rates of competing processes. The novel arylation step is catalyzed by a Pd(OAc)2/NIXANTPHOS-based system via a deprotonative cross-coupling process. The method provides rapid access to skeletally diverse aryl(pyridyl)methanol core structures, which are central components of several medications.
- Gao, Feng,Kim, Byeong-Seon,Walsh, Patrick J.
-
p. 976 - 983
(2016/02/05)
-
- Synthesis of 6-substituted salicylates via biomimetic aromatization utilizing the cross metathesis of a vinyl dioxinone with homoallylic alcohols
-
We herein report biomimetic syntheses of 6-substituted salicylates from the cross metathesis of 2,2-dimethyl-6-vinyl-1,3-dioxin-4-one with homoallylic alcohols, oxidation, and aromatization of the intermediate enone-dioxinones. Of particular note is the u
- Blencowe, Peter S.,Barrett, Anthony G.M.
-
p. 975 - 984
(2013/02/22)
-
- Stereoselective synthesis of optically active cyclopenta[c]pyridines and tetrahydropyridines
-
The intramolecular Pauson-Khand and ring closing metathesis (RCM) reactions of nitrogen containing chiral enynes and dienes are described. The enyne and diene systems comprised of N-propargylated and N-allylated units are constructed on chiral homoallylic
- Sezer, Serdar,Guemruekcue, Yasemin,Bakirci, Irem,Yagiz Uenver,Tanyeli, Cihangir
-
p. 662 - 669
(2012/09/22)
-
- Synthesis, structure and catalytic properties of CNN pincer palladium(II) and ruthenium(II) complexes with N-substituted-2-aminomethyl-6-phenylpyridines
-
N-substituted-2-aminomethyl-6-phenylpyridines 2a-c have been easily prepared from commercially available 6-bromo-2-picolinaldehyde in two steps. Reaction of 2a-c with PdCl2 in toluene in the presence of triethylamine gave the CNN pincer Pd(ii) complexes 3a-c in 18-28% yields. The CNN pincer Ru(ii) complex 5 containing a Ru-NHR functionality could be obtained in a 71% yield by treatment of 2c with a Ru(ii) precursor instead of PdCl 2. Additionally, the related CNN pincer Ru(ii) complex 7 containing a Ru-NH2 functionality has been synthesized by the reaction of 2-aminomethyl-6-phenylpyridine with the same Ru(ii) precursor in a 68% yield. All the new compounds were characterized by elemental analysis (MS for ligands), 1H, 13C NMR, 31P{1H} NMR (for Ru complexes) and IR spectra. Molecular structures of Pd complex 3c as well as Ru complexes 5 and 7 have been determined by X-ray single-crystal diffraction. The obtained Pd complexes 3a-c were effective catalysts for the allylation of aldehydes as well as for three-component allylation of aldehydes, arylamines and allyltributyltin and their activity was found to be much higher than a related NCN Pd(ii) pincer in the allylation of aldehyde. On the other hand, the two new CNN pincer Ru(ii) complexes 5 and 7 displayed excellent catalytic activity in the transfer hydrogenation of ketones in refluxing 2-propanol with the latter being much more active. The final TOF values were up to 4510 h-1 with 0.01 mol% of 5 and 220800 h-1 with 0.005 mol% of 7, respectively. The Royal Society of Chemistry 2011.
- Wang, Tao,Hao, Xin-Qi,Zhang, Xiao-Xue,Gong, Jun-Fang,Song, Mao-Ping
-
experimental part
p. 8964 - 8976
(2011/10/31)
-
- Synthesis and characterization of new (pyrazolyl)aryl phosphinite PCN pincer palladium(II) complexes
-
Two unsymmetrical PCN pincer Pd(II) complexes 3a-3b which are based on (pyrazolyl)aryl phosphinite ligands and contain two fused six-membered palladacycles have been synthesized from 3-(3,5-dimethylpyrazol-1-ylmethyl) benzyl alcohol (2) by one-pot phosphorylation/palladation reaction via C-H bond activation of the related ligands. The pyrazole-coordinated phosphine-free Pd(II) complex (4) was also isolated in the preparation of pincer complex 3a. The new complexes were characterized by elemental analysis, 1H NMR, 13C NMR, 31P {1H} NMR (for pincer complexes) and IR spectra. And the molecular structures of 3b and 4 have been further determined by X-ray single-crystal diffraction. The pincer Pd complexes 3a and 3b exhibited rather low activity in the allylation of benzaldehyde.
- Hou, An-Ting,Liu, Yan-Jing,Hao, Xin-Qi,Gong, Jun-Fang,Song, Mao-Ping
-
supporting information; experimental part
p. 2857 - 2862
(2011/08/10)
-
- Stereoselective synthesis of optically active dihydrofurans and dihydropyrans via a ring closing metathesis reaction
-
A ring closing metathesis reaction of dienes and a ring closing enyne metathesis reaction derived from allyl, homoallyl and homopropargyl alcohol backbones are described. 2-Heteroaryl substituted allyl, homoallyl and homopropargyl alcohols have been easily and efficiently resolved through enzymatic resolution with high ee (93-99%) and known stereochemistry. Enantiomerically enriched dienes derived from allyl and homoallyl alcohols afforded the corresponding enantiomerically enriched dihydrofuran and dihydropyran derivatives, respectively, with chemical yields which varied between 72% and 88%. On the other hand, enantiomerically enriched enynes derived from homoallyl and homopropargyl alcohols gave the corresponding optically active dihydropyrans with conjugated diene units with chemical yields between 70% and 80%. A subsequent Diels-Alder reaction of the dihydropyran derivatives with a diene unit with tetracyanoethylene resulted in the formation of a diastereomeric dihydroisochromene ring system as the sole product.
- Cayir, Merve,Demirci, Sema,Sezer, Serdar,Tanyeli, Cihangir
-
scheme or table
p. 1161 - 1168
(2011/10/13)
-
- Enantioselective addition of allyltin reagents to amino aldehydes catalyzed with bis(oxazolinyl)phenylrhodium(III) aqua complexes
-
Bis(oxazolinyl)phenylrhodium(III) aqua complexes, (Phebox)RhX2 (H2O) [X = Cl, Br], were found to be efficient Lewis acid catalysts for the enantioselective addition of allyl- and methallyltributyltin reagents to amino aldehydes. The
- Motoyama, Yukihiro,Sakakura, Takatoshi,Takemoto, Toshihide,Shimozono, Kayoko,Aoki, Katsuyuki,Nishiyama, Hisao
-
experimental part
p. 5387 - 5401
(2011/09/20)
-
- Homoallylic alcohols via a chemo-enzymatic one-pot oxidation-allylation cascade
-
A chemo-enzymatic one-pot, two-step transformation of (hetero)-benzylic and cinnamic alcohols to yield the elongated homoallylic sec-alcohols in water in up to 96% isolated yield has been developed. The sequence comprised an enzymatic alcohol oxidation using galactose oxidase from Fusarium sp. NRRL 2903 to furnish the corresponding aldehydes, which were subjected directly to allylation via indium(0)-mediated Barbier-type coupling with allyl bromide or by addition of allylboronic acid pinacol ester. Copyright
- Fuchs, Michael,Schober, Markus,Pfeffer, Jan,Kroutil, Wolfgang,Birner-Gruenberger, Ruth,Faber, Kurt
-
p. 2354 - 2358
(2011/10/31)
-
- Carbonyl allylation of aldehydes and ketones with allylic chlorides catalyzed by immobilization of palladium in MCM-41
-
The heterogeneous carbonyl allylation of aldehydes and ketones with allylic chlorides was achieved in DMF using SnCl2 as reducing agent at 25-40 °C in the presence of a 3-(2-aminoethylamino)propyl-functionalized MCM-41-immobilized palladium(II) complex [MCM-41-2N-Pd(II)], yielding a variety of homoallylic alcohols in good to high yields. This heterogeneous palladium catalyst exhibited higher activity than (N-propylethylenediamine)PdCl 2 and can be recovered and recycled by a simple filtration of the reaction solution and used for at least 5 consecutive trials without any decreases in activity.
- Zhao, Hong,Peng, Jian,Xiao, Ruian,Hao, Wenyan,Cai, Ming-Zhong
-
experimental part
p. 2030 - 2034
(2011/06/19)
-
- Ring-closing of 1,7-and 1,8-enynes of propargylic O,O-acetals by ruthenium-catalysed intramolecular metathesis
-
Acyclic 1,7-and 1,8-enynes with the alkyne moiety directly connected to the asymmetric carbon of an ethyl acetal have been obtained in two steps from the corresponding aldehydes. Ring-closing metathesis of these enynes delivered the corresponding six-and
- Lanfranchi, Don Antoine,Bour, Christophe,Boff, Bastien,Hanquet, Gilles
-
experimental part
p. 5232 - 5247
(2010/11/02)
-
- Stereoselective synthesis of optically active cyclopenta[c]pyrans and cyclopenta[c]furans by the intramolecular Pauson-Khand reaction
-
An intramolecular Pauson-Khand reaction of enynes derived from homoallyl, homopropargyl, and allyl alcohols is described. 2-Heteroaryl-substituted homoallyl, homopropargyl, and allyl alcohols are easily and efficiently resolved through enzymatic resolution in high ee (91-99%) and with a known stereochemistry. Each enantiomerically enriched enyne derived from homoallyl and homopropargyl alcohols affords the conformationally most stable diastereomeric cyclopenta[c]pyran ring system as the sole product, whereas enantiomerically enriched enynes derived from allyl alcohols give a diastereomeric cis:trans mixture of the cyclopenta[c]furan ring system.
- Sezer, Serdar,Sahin, Ertan,Tanyeli, Cihangir
-
experimental part
p. 476 - 485
(2010/07/04)
-
- Zn-mediated electrochemical allylation of aldehydes in aqueous ammonia
-
An efficient electrosynthesis of homoallylic alcohols from allylic bromides and aldehydes in aqueous ammonia is achieved in an undivided cell fitted with a pair of zinc electrodes.
- Huang, Jing-Mei,Dong, Yi
-
supporting information; experimental part
p. 3943 - 3945
(2009/12/25)
-
- MACROCYCLIC COMPOUNDS USEFUL AS INHIBITORS OF KINASES AND HSP90
-
Disclosed are macrocyclic compounds of formulae I-V,which are analogs of the pochonin resorcylic acid lactones, and processes for the preparation of the compounds. The compounds disclosed are useful as inhibitors of kinases and Heat Shock Protein 90 (HSP 90). Also disclosed are pharmaceutical compositions comprising an effective kinase-inhibiting amount or an effective HSP90-inhibiting amount of the compounds and methods for the treatment of disorders that are mediated by kinases and HSP90.
- -
-
Page/Page column 102-103
(2010/11/30)
-
- Mild and efficient allylation of aldehydes by using copper fluorapatite as catalyst
-
A facile synthesis of homoallylic alcohols is achieved by the allylation of aldehydes with allylicmetal reagents or allyl halides using copper fluorapatite (CuFAP) as catalyst under mild reaction conditions. A variety of aldehydes were converted to the co
- Lakshmi Kantam,Venkanna,Shiva Kumar,Balasubrahmanyam,Venkateswarlu,Sreedhara
-
experimental part
p. 1497 - 1502
(2009/06/28)
-
- A highly efficient and practical new allylboronate tartramide for the asymmetric allylboration of achiral aldehydes
-
Chiral homoallylic alcohols can be prepared from aldehydes upon reaction with two optically pure allylboronate tartramides. The enantiomeric excess is 10-15% higher for the allylation of benzaldehyde when using N,N'-dibenzyl-tartramide auxiliary 5b than when using N,N'-diphenyl-tartramide (5a). 2-Allyl-N,N'-dibenzyl-1,3,2-dioxaborolane-4,5-dicarbamide (2b) affords homoallylic alcohols with 90-99% ee upon reaction with some representative aldehydes. The derivatised chiral auxiliaries can be recovered by simple recrystallization, in 85% yield, without any loss of specific rotation. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
- Chen, Wansuo,Liu, Yanzhu,Chen, Zhirong
-
p. 1665 - 1668
(2007/10/03)
-
- InCl3-Promoted Allylation of Aldehydes in Ionic Liquid: Scope and Enantioselectivity Studies
-
Indium trichloride was successfully applied to allylation reaction of aldehydes using allytributyltin in ionic liquids. This accelerated catalytic system afforded the allylated products of various aldehydes in moderate to high yields. Preliminary studies
- Lu, Jun,Ji, Shun-Jun,Qian, Rong,Chen, Jian-Ping,Liu, Yu,Loh, Teck-Peng
-
p. 534 - 536
(2007/10/03)
-
- Quinox, a quinoline-type N-oxide, as organocatalyst in the asymmetric allylation of aromatic aldehydes with allyltrichlorosilanes: The role of arene-arene interactions
-
The allylation of aromatic aldehydes with allyltrichlorosilanes can be catalyzed by the new Lewis basic organocatalyst quinox with high enantioselectivity for electron-poor aldehydes and low for their electron-rich congeners (see scheme). This behavior su
- Malkov, Andrei V.,Dufkova, Lenka,Farrugia, Louis,Kocovsky, Pavel
-
p. 3674 - 3677
(2007/10/03)
-
- A Novel Mesoporous Silica-Supported Lewis Acid Catalyst for C-C Bond Formation Reactions in Water
-
Catalytic allylation of carbonyl compounds in water using tetraallyltin in the presence of lanthanum sulfonate immobilized on mesoporous silica (SBA-15) has been carried out for the first time. The reaction proceeded smoothly in water and furnished the co
- Sreekanth, Pentlavalli,Kim, Sang-Wook,Hyeon, Taegwhan,Kim, B. Moon
-
p. 936 - 938
(2007/10/03)
-
- Chemoenzymatic synthesis of optically active heterocyclic homoallylic and homopropargylic alcohols
-
A chemoenzymatic methodology has been developed using indium-mediated allylation of heterocyclic aldehydes under aqueous conditions followed by Pseudomonas cepacia lipase-catalyzed enantioselective acylation of racemic homoallylic and homopropargylic alcohols in organic media. It is observed that the lipase immobilized on ceramic particles (PS-C Amano II) catalyzes the resolution in a highly enantioselective manner in less time as compared to the native enzyme (PS Amano). The approach provides new functionalized chiral synthons useful in the synthesis of natural and pseudonatural products.
- Singh, Satwinder,Kumar, Subodh,Chimni, Swapandeep Singh
-
p. 2679 - 2687
(2007/10/03)
-
- Stereoselective and competitive [1,2]- and [2,3]-wittig rearrangements of allyl heteroarylalkyl ethers
-
Several allyl heteroarylalkyl ethers have been synthesized and then deprotonated with nBuLi in THF at -78°C to give lithium derivatives. The lithium-bearing terminus was either the α- or the α′-carbon atom, depending on the associated proton acidity. In the absence of an external electrophile, a sigmatropic rearrangement occurs, generating a new C-C bond. Heteroarylalkyl homoallylic alcohols and allyl heteroarylalkylic alcohols were obtained as products of stereoselective [2,3]- or [1,2]-Wittig rearrangements, respectively. Homoallylic alcohols were obtained in high yields and with fairly good enantiomeric enrichments when the reactions were carried out in toluene with (-)-sparteine as the external chiral ligand.
- Capriati, Vito,Florio, Saverio,Ingrosso, Giovanni,Granito, Catia,Troisi, Luigino
-
p. 478 - 484
(2007/10/03)
-
- Allylation of carbonyl compounds with allylic gallium reagents
-
Allylic gallium reagents, prepared from gallium trichloride and the corresponding allylic Grignard reagents, allylated carbonyl compounds in good yields in an aqueous medium as well as in organic solvent.
- Tsuji, Takashi,Usugi, Shin-ichi,Yorimitsu, Hideki,Shinokubo, Hiroshi,Matsubara, Seijiro,Oshima, Koichiro
-
-
- InCl3 mediated reactions of aldehydes with allyltrimethylsilane
-
InCl3 mediated coupling reactions of aromatic aldehydes with allyltrimethylsilane readily provide the respective homoallylalcohols and/or the substituted pyran derivatives.
- Ghosh, Rina,Chakraborty, Arijit,De, Debasish,Maiti, Swaraj B.
-
p. 1299 - 1301
(2007/10/03)
-
- Trifluoromethane sulphonic acid: A Bronsted acid catalyst for the addition of allyltributylstannanes to carbonyl compounds in water
-
Trifluoromethane sulphonic acid catalyses the addition of allyltributylstannane to carbonyl compounds in water to give the corresponding homoallylic alcohols in high yields.
- Loh, Teck-Peng,Xu, Jia
-
p. 2431 - 2434
(2007/10/03)
-
- An enantioselective indium-mediated allylation reaction of aldehydes and ketones in dichloromethane
-
An enantioselective indium-mediated addition reaction of allylic bromides to carbonyl compounds was achieved in dichloromethane in the presence of (-)-cinchonidine. The desired products were obtained in moderate to excellent yields and with up to 75% enan
- Loh, Teck-Peng,Zhou, Jian-Rong,Li, Xu-Ran
-
p. 9333 - 9336
(2007/10/03)
-
- Chiral Pyridines: Optical Resolution of 1-(2-Pyridyl)- and 1-[6-(2,2′-Bipyridyl)]ethanols by Lipase-Catalyzed Enantioselective Acetylation
-
The resolution of racemic 1-(2-pyridyl)ethanols 2a-n, including the 2,2′-bipyridyl and isoquinolyl derivatives, by lipase-catalyzed asymmetric acetylation with vinyl acetate is reported. The reactions were carried out in diisopropyl ether at either room temperature or 60°C using Candida antarctica lipase (CAL) to give (R)-acetate and unreacted (S)-alcohol with excellent enantiomeric purities in good yields. The reaction rate was relatively slow at room temperature for substrates bearing an sp3-type carbon at the 6-position on the pyridine ring, such as 2c, 2d, and 2e, and for those bearing 1-hydroxypropyl and allyl groups at the 2-position on the pyridine ring, such as 21 and 2m. In such cases, a higher temperature was required. Thus, when the reaction was conducted at 60°C, it was accelerated 3- to 7-fold without losing the high enantiospecificity. However, the reaction of homoallylic alcohol 2n was not complete, even when the reaction was continued for a longer period of time at 60°C. This enzymatic resolution can be used practically in a wide range of reaction scales from 10 mg to 10 g or more. This catalyst can be used repeatedly with a 5-10% loss of the initial activity with each use.
- Uenishi, Jun'ichi,Hiraoka, Takao,Hata, Shinichiro,Nishiwaki, Kenji,Yonemitsu, Osamu,Nakamura, Kaoru,Tsukube, Hiroshi
-
p. 2481 - 2487
(2007/10/03)
-
- Lewis acid catalysis in aqueous media: Copper(II)-catalyzed aldol and allylation reactions in a water-ethanol-toluene solution
-
Cu(OTf)2 was found to be a stable Lewis acid in aqueous media and to activate carbonyl compounds effectively. Aldol reactions of silyl enol ethers with aldehydes and allylation reactions of tetraallyltin with carbonyl compounds proceeded smooth
- Kobayashi, Shu,Nagayama, Satoshi,Busujima, Tsuyoshi
-
p. 959 - 960
(2007/10/03)
-
- Use of an organometallic reagent in water: Sc(OTf)3-catalyzed allylation reactions of aldehydes in micellar systems
-
The Sc(OTf)3-catalyzed allylation reactions of aldehydes with tetraallyltin proceeded smoothly in micellar systems to afford the corresponding homoallylic alcohols in high yields. The reactions were successfully carried out in the presence of a
- Kobayashi, Shu,Wakabayashi, Takeshi,Oyamada, Hidekazu
-
p. 831 - 832
(2007/10/03)
-
- Aqueous Reactions with a Lewis Acid and an Organometallic Reagent. The Scandium Trifluoromethanesulfonate-Catalyzed Allylation Reaction of Carbonyl Compounds with Tetraallyltin
-
The allylation reaction of a wide variety of carbonyl compounds with tetraallyltin was successfully carried out in aqueous media by using scandium trifluoromethanesulfonate (scandium triflate) as a catalyst.
- Hachiya, Iwao,Kobayashi, Shu
-
p. 6958 - 6960
(2007/10/02)
-
- Chiral Synthesis via Organoboranes. 36. Exceptionally Enantioselective Allylborations of Representative Heterocyclic Aldehydes at -100 deg C under Salt-Free Conditions
-
Chiral terpenyl-based allylborane reagents (Ter2*BCH2CH=CH2, 1-3) undergo facile condensation with representative heterocyclic aldehydes (HetCHO) at -100 deg C (in the absence of Mg2+ salts) and afford the corresponding homoallylic alcohols (HetCH*(OH)CH2CH=CH2, 12-19) in enantiomeric purities approaching 100percent ee.A new workup procedure involving 8-hydroxyquinoline (8-HQ) has been utilized for the convenient isolation of the product alcohols.
- Racherla, Uday S.,Liao, Yi,Brown, Herbert C.
-
p. 6614 - 6617
(2007/10/02)
-