102632-99-5Relevant articles and documents
Allylsamarium bromide-mediated cascade cyclization of homoallylic esters. Synthesis of 2-(2-hydroxyalkyl)cyclopropanols and 2-(2-hydroxyethyl)bicyclo[2.1.1]hexan-1-ols
Shen, Mengmeng,Tu, Yawei,Xie, Guanqun,Niu, Qingsheng,Mao, Hui,Xie, Tingting,Flowers, Robert A.,Lv, Xin,Wang, Xiaoxia
, p. 52 - 61 (2015)
In continuation of our previous study on the intramolecular reductive coupling of simple homoallylic esters promoted by allylSmBr/HMPA/H2O, which afforded a facile synthesis of 2-(2-hydroxyalkyl)cyclopropanols, here we report the reductive casc
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Lansbury,P.T.,Pattison,V.A.
, p. 4295 - 4298 (1962)
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Synthesis of a trans-chelating chiral diphosphine ligand with only planar chirality and its application to asymmetric hydrosilylation of ketones
Kuwano,Uemura,Saitoh,Ito
, p. 1327 - 1330 (1999)
Optically active diphosphine (S,S)-2,2-bis[(diethylphosphino)methyl]- 1,1-biferrocene (abbreviated to (S,S)-EtTRAP-H) was synthesized from ferrocenyloxazoline derived from-L-valinol in 47% overall yield. The new chiral ligand, (S,S)-EtTRAP-H, which coordinates to a rhodium atom in a trans-chelating manner, was effective for asymmetric hydrosilylation of ketones to give optically active secondary alcohols with up to 94% ee.
Easy selective generation of (lithiomethyl)cyclopropane or homoallyllithium by a chlorine-lithium exchange
Pastor, Isidro M.,Pe?afiel, Itziar,Yus, Miguel
, p. 6870 - 6872 (2008)
The reaction of (chloromethyl)cyclopropane 5 with lithium and a catalytic amount of DTBB (5 mol %) in the presence of different carbonyl compounds [Et2CO, n-Pr2CO, (c-C3H5)2CO, (CH2)5CO, PhCOMe, t-BuCHO, i-PrCHO, PhCHO] as electrophiles in THF at -78 °C leads, after hydrolysis with water, to the corresponding cyclopropyl alcohols 6. However, when the same starting material is lithiated using naphthalene as the arene catalyst in ether at 0 °C and then reacts with the same series of electrophiles, the final hydrolysis with water yields the corresponding unsaturated alcohols 7.
Allylation of epoxides with allylic indium reagents
Hirashita, Tsunehisa,Mitsui, Kazuma,Hayashi, Yousuke,Araki, Shuki
, p. 9189 - 9191 (2004)
Allylindium sesquihalide reacts with epoxide to give homoallyl alcohol via a 1,2-shift reaction. In contrast, allylindate gives the ring-opening product without rearrangement.
Yb(OTf)3 catalyzed highly regioselective allylation of aromatic epoxides: An efficient route to bishomoallyl alcohols
Likhar, Pravin R.,Kumar, Manyam Praveen,Bandyopadhyay, Ananda K.
, p. 3333 - 3335 (2002)
Anhydrous ytterbium(III) triflate-catalyzed ring opening of aromatic 1,2-epoxides with allyltributyltin in THF results in the formation of bishomoallyl alcohols in excellent yields and with complete regioselectivity. The results are compared with those ob
Highly Enantioselective Construction of Dihydrooxazines via Pd-Catalyzed Asymmetric Carboetherification
Li, Na,Sun, Baozhen,Liu, Shuang,Zhao, Jinbo,Zhang, Qian
supporting information, p. 190 - 193 (2020/01/02)
A straightforward synthesis of highly enantioenriched 5,6-dihydro-4H-1,2-oxazines is realized by Pd-catalyzed asymmetric carboetherification of γ,δ-alkenyl oximes with (hetero)aryl and alkenyl halides in the presence of a commercially available bisphosphine ligand. The enantioenriched products can be facilely converted to functionalized alcohols with high fidelity of chiral transfer.
Copper-Catalyzed Cope-Type Hydroamination of Nonactivated Olefins toward Cyclic Nitrones: Scope, Mechanism, and Enantioselective Process Development
Zhang, Mengru,Liu, Shuang,Li, Hexin,Guo, Yajing,Li, Na,Guan, Meihui,Mehfooz, Haroon,Zhao, Jinbo,Zhang, Qian
supporting information, p. 12620 - 12627 (2019/09/16)
The catalytic synthesis of cyclic nitrones, an important type of functional molecules for both synthetic chemistry and related fields, remains underdeveloped. Herein we report the copper-catalyzed Cope-type hydroamination of oximes with pendant nonactivated olefins, which enables facile access to a series of five- and six-membered cyclic nitrones under mild conditions. In this study, heterocycle-tethered oximes were employed in the Cope-type hydroamination reaction for the first time. High enantioselectivity was achieved for carbon-tethered γ,δ-vinyl oximes to afford enantioenriched five-membered cyclic nitrones. The results of preliminary mechanistic studies indicate a mononuclear catalytic species and a unified catalytic pathway over a large temperature range.