CATALYTIC ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION OF AZOMETHINE IMINES TO ALLYL ALCOHOL UTILIZING TARTARIC ACID ESTER AS A CHIRAL AUXILIARY

被引：19

作者：

Tanaka, Katsuyoshi ^{[1
]}

Kato, Tomomitsu ^{[1
]}

Ukaji, Yutaka ^{[1
]}

Inomata, Katsuhiko ^{[1
]}

机构：

[1] Kanazawa Univ, Grad Sch Nat Sci & Technol, Div Mat Sci, Kanazawa, Ishikawa 9201192, Japan

来源：

HETEROCYCLES | 2010年 / 80卷 / 02期

基金：

日本学术振兴会;

关键词：

Enantioselective 1,3-Dipolar Cycloaddition; Azomethine Imine; Optically Active Pyrazolidine; Magnesium Bromide; Diisopropyl; (R; R)-Tartrate; NITRONE CYCLOADDITIONS; LEWIS-ACID; MAGNESIUM; ACCELERATION; REGIOCONTROL; OXIDE;

D O I：

10.3987/COM-09-S(S)116

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic regio- and enantioselective 1,3-dipolar cycloaddition of azomethine imines to allyl alcohol was achieved by utilizing diisopropyl (R,R)-tartrate as a chiral auxiliary to afford the corresponding optically active trans-pyrazolidines with enantioselectivities up to 93% ee. Addition of MgBr2 was crucial to realize reproducible high enantioselectivity.

引用

页码：887 / 893

页数：7

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