Catalytic asymmetric synthesis of a nitrogen analogue of dialkyl tartrate by direct Mannich reaction under phase-transfer conditions

被引：125

作者：

Ooi, T ^{[1
]}

Kameda, M ^{[1
]}

Fujii, J ^{[1
]}

Maruoka, K ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 14期

关键词：

D O I：

10.1021/ol049215u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Phase-transfer-catalyzed direct Mannich reaction of glycinate Schiff base 3 with alpha-imino ester 4 has been accomplished with high enantioselectivity by the utilization of N-spiro C-2-symmetric chiral quaternary ammonium bromide 2 as a catalyst. This methodology enables the catalytic asymmetric synthesis of differentially protected 3-aminoaspartate, a nitrogen analogue of dialkyl tartrate. The product (syn-5) was converted into a precursor (6) of streptolidine lactam.

引用

页码：2397 / 2399

页数：3

共 29 条

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