Silver/ThioClickFerrophos-Catalyzed Enantioselective Conjugate Addition and Cycloaddition of Glycine Imino Ester with Nitroalkenes

被引：58

作者：

Imae, Kazumi ^{[1
]}

Konno, Takashi ^{[1
]}

Ogata, Kenichi ^{[1
]}

Fukuzawa, Shin-ichi ^{[1
]}

机构：

[1] Chuo Univ, Dept Appl Chem, Inst Sci & Engn, Bunkyo Ku, Tokyo 1128551, Japan

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 17期

基金：

日本学术振兴会;

关键词：

ASYMMETRIC MICHAEL REACTION; ALPHA-AMINO-ACIDS; 1,3-DIPOLAR CYCLOADDITION; AZOMETHINE YLIDES; ALDOL REACTIONS; SCHIFF-BASE; 1,4-ADDITION; DERIVATIVES; ORIGINS;

D O I：

10.1021/ol301916t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We applied the combination of AgOAc with ThioClickFerrophos, the chiral ferrocenyl triazole-based P,S-ligand, to the reaction of glycine imino ester with nitroalkenes. The conjugate addition of the imino methyl ester preferentially produced anti-alpha-imino-gamma-nitrobutyrates in good yields with high enantioselectivities (ee) of up to 99% at -25 degrees C in THF in the presence of triethylamine. Meanwhile, the pyrrolidine cycloadducts were obtained as major products in good yields with high enantioselectivities (up to 96% ee) using tert-butyl imino ester in the absence of triethylamine at room temperature.

引用

页码：4410 / 4413

页数：4

共 38 条

[1] Synthesis of a novel crown ether derived from chiro-inositol and its catalytic activity on the asymmetric Michael addition [J].

Akiyama, T ;

Hara, M ;

Fuchibe, K ;

Sakamoto, S ;

Yamaguchi, K .

CHEMICAL COMMUNICATIONS, 2003, (14) :1734-1735

[2] Phase-transfer-catalyzed asymmetric Michael reaction using newly-prepared chiral quaternary ammonium salts derived from L-tartrate [J].

Arai, S ;

Tsuji, R ;

Nishida, A .

TETRAHEDRON LETTERS, 2002, 43 (52) :9535-9537

[3] Stereocontrolled synthesis of highly substituted proline esters via [3+2] cycloaddition between N-metalated azomethine ylides and nitroalkenes.: Origins of the metal effect on the stereochemical outcome [J].

Ayerbe, M ;

Arrieta, A ;

Cossío, FP ;

Linden, A .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (06) :1795-1805

[4]

Berner OM, 2002, EUR J ORG CHEM, V2002, P1877

[5] In the golden age of organocatalysis [J].

Dalko, PI ;

Moisan, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175

[6] Highly enantioselective asymmetric 1,3-dipolar cycloaddition of azomethine ylide catalyzed by a copper(I)/ClickFerrophos complex [J].

Fukuzawa, Shin-ichi ;

Oki, Hiroshi .

ORGANIC LETTERS, 2008, 10 (09) :1747-1750

[7] Catalytic asymmetric direct Mannich reaction: a powerful tool for the synthesis of α,β-diamino acids [J].

Gomez Arrayas, Ramon ;

Carretero, Juan C. .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (07) :1940-1948

[8]

Hashimoto T., 2010, HDB CYCLIZATION REAC, V1, P87

[9] Recent development and application of chiral phase-transfer catalysts [J].

Hashimoto, Takuya ;

Maruoka, Keiji .

CHEMICAL REVIEWS, 2007, 107 (12) :5656-5682

[10] Enantiocontrolled Synthesis of β-Branched α-Amino Acids by Using CuI-Catalyzed 1,4-Addition of Glycine Imines to β-Substituted gem-Diactivated Olefins [J].

Hernandez-Toribio, Jorge ;

Gomez Arrayas, Ramon ;

Carretero, Juan C. .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (23) :6334-6337

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