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

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