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

[1] Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene
Alexakis, A
Andrey, O
[J]. ORGANIC LETTERS, 2002, 4 (21) : 3611 - 3614
[2] Organocatalytic asymmetric conjugate additions
Almasi, Diana
Alonso, Diego A.
Najera, Carmen
[J]. TETRAHEDRON-ASYMMETRY, 2007, 18 (03) : 299 - 365
[3] Chiral piperazines as efficient catalysts for the asymmetric Michael addition of aldehydes to nitroalkenes
Barros, Maria Teresa
Phillips, Ana Maria Faisca
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (01) : 178 - 185
[4] Berner OM, 2002, EUR J ORG CHEM, V2002, P1877
[5] Synthesis and in vivo evaluation of 3-substituted gababutins
Blakemore, David C.
Bryans, Justin S.
Carnell, Pauline
Chessum, Nicola E. A.
Field, Mark J.
Kinsella, Natasha
Kinsora, Jack K.
Osborne, Simon A.
Williams, Sophie C.
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (01) : 362 - 365
[6] Blakemore DC, 2010, BIOORG MED CHEM LETT, V20, P248, DOI 10.1016/j.bmcl.2009.10.121
[7] Sequential Organocatalyzed Michael Addition/[3+2]-Heterocyclization for the Stereoselective Synthesis of Fused-Isoxazoline Precursors of Enantiopure Cyclopentanoids
Bonne, Damien
Salat, Lydie
Dulcere, Jean-Pierre
Rodriguez, Jean
[J]. ORGANIC LETTERS, 2008, 10 (23) : 5409 - 5412
[8] An in vitro investigation into conformational aspects of gabapentin
Bryans, JS
Horwell, DC
Ratcliffe, GS
Receveur, JM
Rubin, JR
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (05) : 715 - 721
[9] Proline-based reduced dipeptides as recyclable and highly enantioselective organocatalysts for asymmetric Michael addition
Cao, Xiaohui
Wang, Ge
Zhang, Richeng
Wei, Yingying
Wang, Wei
Sun, Huichao
Chen, Ligong
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (19) : 6487 - 6490
[10] Pyrrolidine-Camphor Derivative as an Organocatalyst for Asymmetic Michael Additions of α,α-Disubstituted Aldehydes to β-Nitroalkenes: Construction of Quaternary Carbon-Bearing Aldehydes under Solvent-Free Conditions
Chang, Chihliang
Li, Ssu-Hsien
Reddy, Raju Jannapu
Chen, Kwunmin
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (09) : 1273 - 1278

← 1 2 3 4 5 6 →