anti-Selective direct asymmetric Mannich reactions catalyzed by axially chiral amino sulfonamide as an organocatalyst

被引：195

作者：

Kano, T ^{[1
]}

Yamaguchi, Y ^{[1
]}

Tokuda, O ^{[1
]}

Maruoka, K ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 47期

关键词：

D O I：

10.1021/ja056008w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A direct asymmetric Mannich reaction using a novel axially chiral amino trifluoromethanesulfonamide (S)-3 has been developed in highly anti-selective and enantioselective manners. Thus, in the presence of a catalytic amount of (S)-3, the reactions between aldehydes and the α-imino ester 4 proceed smoothly to give the functional β-amino aldehydes with significantly higher anti/syn ratio and enantioselectivity than previously possible. Copyright © 2005 American Chemical Society.

引用

页码：16408 / 16409

页数：2

共 27 条

[1] Catalytic asymmetric Mannich reactions of glycine derivatives with imines.: A new approach to optically active α,β-diamino acid derivatives [J].

Bernardi, L ;

Gothelf, AS ;

Hazell, RG ;

Jorgensen, KA .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07) :2583-2591

[2] Organocatalysis with proline derivatives: improved catalysts for the asymmetric Mannich, nitro-Michael and aldol reactions [J].

Cobb, AJA ;

Shaw, DM ;

Longbottom, DA ;

Gold, JB ;

Ley, SV .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (01) :84-96

[3] The direct catalytic asymmetric cross-Mannich reaction:: A highly enantioselective route to 3-amino alcohols and α-amino acid derivatives [J].

Córdova, A .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (08) :1987-1997

[4] The direct catalytic asymmetric Mannich reaction [J].

Córdova, A .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (02) :102-112

[5] anti-selective SMP-catalyzed direct asymmetric Mannich-type reactions:: synthesis of functionalized amino acid derivatives [J].

Córdova, A ;

Barbas, CF .

TETRAHEDRON LETTERS, 2002, 43 (43) :7749-7752

[6] A highly enantioselective route to either enantiomer of both α- and β-amino acid derivatives [J].

Córdova, A ;

Watanabe, S ;

Tanaka, F ;

Notz, W ;

Barbas, CF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) :1866-1867

[7] A highly enantioselective amino acid-catalyzed route to functionalized α-amino acids [J].

Córdova, A ;

Notz, W ;

Zhong, GF ;

Betancort, JM ;

Barbas, CF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) :1842-1843

[8] Asymmetric synthesis of selectively protected amino sugars and derivatives by a direct organocatalytic Mannich reaction [J].

Enders, D ;

Grondal, C ;

Vrettou, M ;

Raabe, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (26) :4079-4083

[9] Highly enantioselective synthesis of fluorinated γ-amino alcohols through proline-catalyzed cross-Mannich reaction [J].

Fustero, S ;

Jiménez, D ;

Sanz-Cervera, JF ;

Sánchez-Roselló, M ;

Esteban, E ;

Simón-Fuentes, A .

ORGANIC LETTERS, 2005, 7 (16) :3433-3436

[10] The direct and enantioselective, one-pot, three-component, cross-Mannich reaction of aldehydes [J].

Hayashi, Y ;

Tsuboi, W ;

Ashimine, I ;

Urushima, T ;

Shoji, M ;

Sakai, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) :3677-3680

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