Enantioselective synthesis of gabapentin analogues via organocatalytic asymmetric Michael addition of α-branched aldehydes to β-nitroacrylates

被引：40

作者：

Yoshida, Masanori ^{[1
,2
]}

Masaki, Erika ^{[3
]}

Ikehara, Hiroto ^{[2
]}

Hara, Shoji ^{[1
,2
]}

机构：

[1] Hokkaido Univ, Fac Engn, Div Chem Proc Engn, Kita Ku, Sapporo, Hokkaido 0608628, Japan

[2] Hokkaido Univ, Grad Sch Chem Sci & Engn, Mol Chem & Engn Course, Kita Ku, Sapporo, Hokkaido 0608628, Japan

[3] Hokkaido Univ, Sch Engn, Dept Appl Sci & Engn, Kita Ku, Sapporo, Hokkaido 0608628, Japan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 27期

关键词：

HIGHLY EFFICIENT; ALPHA; ALPHA-DISUBSTITUTED ALDEHYDES; 1,4-ADDITION REACTIONS; CONJUGATE ADDITION; AMINO-ACID; CATALYSTS; KETONES; NITROALKENES; ISOBUTYRALDEHYDE; NITROETHYLENE;

D O I：

10.1039/c2ob25413a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Michael addition reaction of alpha-branched aldehydes to beta-nitroacrylates was successfully carried out by using a mixed catalyst consisting of a primary amino acid, L-phenylalanine, and its lithium salt to give beta-formyl-beta'-nitroesters having a quaternary carbon centre in good yields (up to 85%) with high enantioselectivity (up to 98% ee). By using benzyl beta-nitroacrylates as Michael acceptors, the obtained beta-formyl-beta'-nitroesters were converted into various 4,4-disubstituted pyrrolidine-3-carboxylic acids including analogues of gabapentin (Neurotin(R)) in one step from the Michael adducts in high yields.

引用

页码：5289 / 5297

页数：9

共 55 条

[11] Pyrrolidinyl-sulfamide derivatives as a new class of bifunctional organocatalysts for direct asymmetric Michael addition of cyclohexanone to nitroalkenes
Chen, Jia-Rong
Fu, Liang
Zou, You-Quan
Chang, Ning-Jie
Rong, Jian
Xiao, Wen-Jing
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (14) : 5280 - 5287
[12] The development of asymmetric primary amine catalysts based on cinchona alkaloids
Chen, Ying-Chun
[J]. SYNLETT, 2008, (13) : 1919 - 1930
[13] The synthesis of baclofen and GABOB via Rh(II) catalyzed intramolecular C-H insertion of α-diazoacetamides
Chen, ZL
Chen, ZY
Jiang, YZ
Hu, WH
[J]. TETRAHEDRON, 2005, 61 (06) : 1579 - 1586
[14] Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene:: Efficient access to γ2-amino acids
Chi, Yonggui
Guo, Li
Kopf, Nathan A.
Gellman, Samuel H.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (17) : 5608 - +
[15] Asymmetric Organocatalytic Reactions of α,β-Unsaturated Cyclic Ketones
Dalpozzo, Renato
Bartoli, Giuseppe
Bencivenni, Giorgio
[J]. SYMMETRY-BASEL, 2011, 3 (01): : 84 - 125
[16] Self-assembly of organocatalysts for the enantioselective Michael addition of aldehydes to nitroalkenes
Demir, Ayhan S.
Eymur, Serkan
[J]. TETRAHEDRON-ASYMMETRY, 2010, 21 (01) : 112 - 115
[17] Catalytic asymmetric Michael reactions of acetaldehyde
Garcia-Garcia, Patricia
Ladepeche, Arnaud
Halder, Rajkumar
List, Benjamin
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (25) : 4719 - 4721
[18] Stereospecific Synthesis of Conformationally Constrained γ-Amino Acids: New Foldamer Building Blocks That Support Helical Secondary Structure
Guo, Li
Chi, Yonggui
Almeida, Aaron M.
Guzei, Ilia A.
Parker, Brian K.
Gellman, Samuel H.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (44) : 16018 - +
[19] Asymmetric Michael reaction of acetaldehyde catalyzed by diphenylprolinol silyl ether
Hayashi, Yujiro
Itoh, Takahiko
Ohkubo, Masahiro
Ishikawa, Hayato
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (25) : 4722 - 4724
[20] Bifunctional Transition Metal-Based Molecular Catalysts for Asymmetric C-C and C-N Bond Formation
Ikariya, Takao
Gridnev, Ilya D.
[J]. TOPICS IN CATALYSIS, 2010, 53 (13-14) : 894 - 901

← 1 2 3 4 5 6 →