109801-00-5Relevant academic research and scientific papers
Synthesis of highly decorated chiral 2-nitro-cyclohexane carboxylic esters through microwave-assisted organocatalyzed cascade reactions
Massolo, Elisabetta,Benaglia, Maurizio,Parravicini, Davide,Brenna, Davide,Annunziata, Rita
, p. 6639 - 6642 (2014)
Starting from (E)-β-substituted-β-nitroacrylates and α,β-unsaturated ketones, a stereoselective organocatalyzed one-pot methodology allowed to synthesize highly decorated chiral 2-nitro-cyclohexane carboxylic esters. The reaction is promoted by Cinchona a
Conjugate allylation to α,β-unsaturated aldehydes with the new chemzyme p-F-ATPH
Ooi,Kondo,Maruoka
, p. 1183 - 1185 (1997)
Success at last: The 1,4-allylation of α,β-unsaturated aldehydes with selectivities up to 95/5 and yields of 83% has been achieved thanks to the newly developed Lewis acidic receptor p-F-ATPH (L= 2,6-(p-FC6H4)2C6H3O). In addition to a coordination site for the aldehyde, this possesses an appropriate coordination site for a reactive nucleophile, as shown schematically on the right.
Alkylation of unsaturated aldehyde and allylic bisacetate with organomanganese reagents in presence of tetrakis acetonitrile copper(I) tetrafluroborate
Deshmukh,Jadhav,Mali,Suryawanshi,Anbhule,Jagtap,Deshmukh
, p. 2967 - 2971 (2005)
The conjugate addition of organomanganese reagents to α,β- unsaturated aldehydes and allylic bisacetate in presence of Me3Si-Cl and tetrakis acetonitrile copper(I) tetrafluroborate is described. Copyright Taylor & Francis, Inc.
Evaluation of several fluorinated ATPH derivatives as functionalized Lewis acid receptors for conjugate alkylation to α,β-unsaturated aldehydes with alkyllithium nucleophiles
Ooi, Takashi,Kondo, Yuichiro,Miura, Tomoya,Maruoka, Keiji
, p. 3951 - 3954 (1997)
Several fluorinated aluminum tris(2,6-diphenylphenoxide) (ATPH) derivatives have been synthesized to evaluate, as functionalized Lewis acid receptors, the conjugate alkylation ability to α,β-unsaturated aldehydes by the combined use of alkyllithium nucleo
Accessing Both Retention and Inversion Pathways in Stereospecific, Nickel-Catalyzed Miyaura Borylations of Allylic Pivalates
Zhou, Qi,Srinivas, Harathi D.,Zhang, Songnan,Watson, Mary P.
supporting information, p. 11989 - 11995 (2016/10/07)
We have developed a stereospecific, nickel-catalyzed Miyaura borylation of allylic pivalates, which delivers highly enantioenriched α-stereogenic γ-aryl allylboronates with good yields and regioselectivities. Our complementary sets of conditions enable access to either enantiomer of allylboronate product from a single enantiomer of readily prepared allylic pivalate substrate. Excellent functional group tolerance, yields, regioselectivities, and stereochemical fidelities are observed. The stereochemical switch from stereoretention to stereoinversion largely depends upon solvent and can be explained by competitive pathways for the oxidative addition step. Our mechanistic investigations support a stereoretentive pathway stemming from a directed oxidative addition and a stereoinvertive pathway that is dominant when MeCN blocks coordination of the directing group by binding the nickel catalyst.
Catalytic asymmetric addition of aldehydes using organolithium reagents in the presence of commercial available chiral diol ligands
Zong, Hua,Huang, Huayin,Song, Ling
supporting information, p. 1069 - 1074 (2016/10/11)
An efficient method for the catalytic asymmetric additions to aldehydes using organolithium reagents and titanium(IV) isopropoxide in the presence of commercially available and relatively inexpensive diol ligands, such as (S)-BINOL or D-TADDOL has been developed. Good to excellent yields (up to 92%) and enantioselectivities (up to 94%) of the corresponding secondary alcohol products can be obtained following a simple procedure at relatively mild reaction temperatures.
Pincer-Nickel-Catalyzed Allyl-Aryl Coupling between Allyl Methyl Ethers and Arylzinc Chlorides
Tao, Jian-Long,Yang, Bo,Wang, Zhong-Xia
, p. 12627 - 12634 (2016/01/09)
The P,N,N-pincer nickel complex [Ni(Cl){N(2-Ph2PC6H4)(2′-Me2NC6H4)}]-catalyzed allyl-aryl coupling was studied. The reaction of allyl methyl ethers, including (1-methoxyallyl)arenes and (3-methoxyprop-1-en-1-yl)arenes, with arylzinc chlorides afforded linear (E)-alkenes in high yields, whereas the reaction of (E)-1-methoxytridec-2-ene with p-Me2NC6H4ZnCl generated a mixture of linear and branched alkenes.
1,n-rearrangement of allylic alcohols promoted by hot water: Application to the synthesis of navenone B, a polyene natural product
Li, Pei-Fang,Wang, Heng-Lu,Qu, Jin
, p. 3955 - 3962 (2014/05/20)
It was reported for the first time that hot water as a mildly acidic catalyst efficiently promoted 1,n-rearrangement (n = 3, 5, 7, 9) of allylic alcohols. In some cases, the rearrangement reactions joined isolated C-C double or triple bonds to generate conjugated polyene or enyne structure motifs. We used the 1,3-rearrangement reaction of an allylic alcohol in hot water as part of an attractive new strategy for construction of the polyene natural product navenone B by iterative use of a Grignard reaction, a 1,3-rearrangement of the resulting allylic alcohol, and subsequent oxidation of the rearranged product.
Pd-Catalyzed stereospecific allyl-aryl coupling of allylic alcohols with arylboronic acids
Ye, Jiang,Zhao, Jingming,Xu, Jing,Mao, Yuxue,Zhang, Yong Jian
supporting information, p. 9761 - 9763 (2013/10/21)
An efficient method for Pd-catalyzed stereospecific allyl-aryl coupling of allylic alcohols with arylboronic acids has been described. The reactions proceeded smoothly in the presence of Pd2(dba)3· CHCl3 and racemic BINAP
Room temperature and highly enantioselective additions of alkyltitanium reagents to aldehydes catalyzed by a titanium catalyst of (R)-h 8-binol
Li, Qinghan,Gau, Han-Mou
experimental part, p. 929 - 939 (2012/06/29)
Three alkyltitanium reagents of RTi(O-i-Pr)3 (R = Cy (1a), i-Bu (1b), and n-Bu (1c)) were prepared in good yields. The high-resolution mass spectroscopy showed that 1b and 1c in the gas phase are monomeric species. However, the solid state of 1a revealed a dimeric structure. Asymmetric additions of 1a-1c to aldehydes catalyzed by a titanium catalyst of (R)-H 8-BINOL were studied at room temperature. The reactions produced desired secondary alcohols in good yields with good to excellent enantioselectivities of up to 94% ee. Reactivity and enantioselectivity differences, in terms of steric bulkiness of the R nucleophiles, are herein described. The addition reactions of secondary c-hexyl to aldehydes were slower than the reactions of primary i-butyl or n-butyl nucleophiles. For the primary alkyls, lower enantioselectivities were obtained for products from addition reactions of the linear n-butyl as compared with the enantioselectivities of products from the addition reactions of the branched i-butyl group. The same stereochemistry of RTi(O-i-Pr)3 addition reactions as the addition reactions of organozinc, organoaluminum, Grignard, or organolithium reagents directly supports the argument of that titanium-catalyzed addition reactions of aldehydes involve an addition of an organotitanium nucleophile.
