Organocatalytic asymmetric nitrocyclopropanation of α,β-unsaturated aldehydes

被引：75

作者：

Vesely, Jan ^{[1
]}

Zhao, Gui-Ling ^{[1
]}

Bartoszewicz, Agnieszka ^{[1
]}

Cordova, Armando ^{[1
]}

机构：

[1] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 27期

关键词：

D O I：

10.1016/j.tetlet.2008.04.162

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel organocatalytic highly enantioselective nitrocyclopropanation reaction of alpha,beta-unsaturated aldehydes is presented. The 1-nitro-2-formylcyclopropane derivatives synthesized from this catalytic transformation were converted to the corresponding beta-nitromethyl-acid esters, which are excellent precursors of GABA analogues such as Baclofen, by subsequent organocatalytic chemoselective ring-opening. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：4209 / 4212

页数：4

共 60 条

[1] Catalytic, asymmetric sulfur ylide-mediated epoxidation of carbonyl compounds: Scope, selectivity, and applications in synthesis [J].

Aggarwal, VK ;

Winn, CL .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :611-620

[2]

Aggarwal VK, 2001, ANGEW CHEM INT EDIT, V40, P1433, DOI 10.1002/1521-3773(20010417)40:8<1433::AID-ANIE1433>3.0.CO

[3]

2-E

[4] Diastereoselective conjugate addition of cyanide to α,β-unsaturated oxazolidinones:: Enantioselective synthesis of ent-pregabalin and baclofen [J].

Armstrong, Alan ;

Convine, Nicola J. ;

Popkin, Matthew E. .

SYNLETT, 2006, (10) :1589-1591

[5] Conjugate additions of nitroalkanes to electron-poor alkenes: Recent results [J].

Ballini, R ;

Bosica, G ;

Fiorini, D ;

Palmieri, A ;

Petrini, M .

CHEMICAL REVIEWS, 2005, 105 (03) :933-971

[6] A general procedure for the one-pot preparation of polyfunctionalized nitrocyclopropanes [J].

Ballini, R ;

Fiorini, D ;

Palmieri, A .

SYNLETT, 2003, (11) :1704-1706

[7] Synthesis of both enantiomers of baclofen using (R)- and (S)-N-phenylpantolactam as chiral auxiliaries [J].

Camps, P ;

Muñoz-Torrero, D ;

Sánchez, L .

TETRAHEDRON-ASYMMETRY, 2004, 15 (13) :2039-2044

[8] Stereoselective synthesis of quaternary α-amino acids.: Part 2.: Cyclic compounds [J].

Cativiela, C ;

Díaz-de-Villegas, MD .

TETRAHEDRON-ASYMMETRY, 2000, 11 (03) :645-732

[9] Catalytic asymmetric cyclopropanation of allylic alcohols with titanium-TADDOLate: Scope of the cyclopropanation reaction [J].

Charette, AB ;

Molinaro, C ;

Brochu, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (49) :12168-12175

[10] TOTAL SYNTHESIS OF DL-SIRENIN [J].

COREY, EJ ;

ACHIWA, K ;

KATZENEL.JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (15) :4318-&

← 1 2 3 4 5 6 →