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
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
收藏
页码:5289 / 5297
页数:9
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