ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION REACTIONS OF AZOMETHINE IMINES WITH ACROLEIN CATALYZED BY L-PROLINE AND ITS DERIVATIVES

被引：35

作者：

Suga, Hiroyuki ^{[1
]}

Arikawa, Tadashi ^{[1
]}

Itoh, Kennosuke ^{[1
]}

Okumura, Yukihisa ^{[1
]}

Kakehi, Akikazu ^{[1
]}

Shiro, Motoo ^{[2
]}

机构：

[1] Shinshu Univ, Dept Chem & Mat Engn, Fac Engn, Nagano 3808553, Japan

[2] Rigaku Corp, Tokyo 1968666, Japan

来源：

HETEROCYCLES | 2010年 / 81卷 / 07期

关键词：

CHIRAL LEWIS-ACIDS; ALPHA-AMINO-ACIDS; ALPHA; BETA-UNSATURATED ALDEHYDES; BINAPHTHYLDIIMINE-NI(II) COMPLEXES; NITRONES; YLIDES; ORGANOCATALYSTS; EXO;

D O I：

10.3987/COM-10-11967

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,3-Dipolar cycloadditions between acrolein and various N,N'-cyclic azomethine imines in the presence of L-proline and its derivatives as organocatalysts were investigated. Reactions that were catalyzed by (S)-indline-2-carboxylic acid (30 mol%) in CHCl(3)/MeOH 97:3 (v/v) showed high exo-selectivities (exolendo 91:9 similar to 99:1) and enantioselectivities (75 similar to 98% ee). In contrast, reactions catalyzed by L-proline (30 mol%) under similar conditions favored the endo-cycloadduct (83:27 similar to 99:1) with modest to good enantioselectivities (31 similar to 83% ee). Based on our studies, the diastereoselective mechanism of the L-proline-catalyzed reaction was found to involve the isomerization of the exo- to the endo-cycloadduct in the presence of L-proline.

引用

页码：1669 / 1688

页数：20

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