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 [J].

Alexakis, A ;

Andrey, O .

ORGANIC LETTERS, 2002, 4 (21) :3611-3614

[2] Organocatalytic asymmetric conjugate additions [J].

Almasi, Diana ;

Alonso, Diego A. ;

Najera, Carmen .

TETRAHEDRON-ASYMMETRY, 2007, 18 (03) :299-365

[3] Chiral piperazines as efficient catalysts for the asymmetric Michael addition of aldehydes to nitroalkenes [J].

Barros, Maria Teresa ;

Phillips, Ana Maria Faisca .

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 [J].

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. .

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 [J].

Bonne, Damien ;

Salat, Lydie ;

Dulcere, Jean-Pierre ;

Rodriguez, Jean .

ORGANIC LETTERS, 2008, 10 (23) :5409-5412

[8] An in vitro investigation into conformational aspects of gabapentin [J].

Bryans, JS ;

Horwell, DC ;

Ratcliffe, GS ;

Receveur, JM ;

Rubin, JR .

BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (05) :715-721

[9] Proline-based reduced dipeptides as recyclable and highly enantioselective organocatalysts for asymmetric Michael addition [J].

Cao, Xiaohui ;

Wang, Ge ;

Zhang, Richeng ;

Wei, Yingying ;

Wang, Wei ;

Sun, Huichao ;

Chen, Ligong .

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 [J].

Chang, Chihliang ;

Li, Ssu-Hsien ;

Reddy, Raju Jannapu ;

Chen, Kwunmin .

ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (09) :1273-1278

← 1 2 3 4 5 6 →