Revisiting optically active quaternary derivatives made from prolinol as phase transfer catalysts

被引：17

作者：

Dehmlow, EV ^{[1
]}

Klauck, R ^{[1
]}

Düttmann, S ^{[1
]}

Neumann, B ^{[1
]}

Stammler, HG ^{[1
]}

机构：

[1] Univ Bielefeld, Fak Chem, D-33501 Bielefeld, Germany

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 13期

关键词：

D O I：

10.1016/S0957-4166(98)00213-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

New non-racemic ammonium salts derived from prolinol have been prepared which are stereogenic both at N and at C. Absolute configurations rest on X-ray structures for 3c and 7a. The new compounds have been tested in a number of known enantioselective phase transfer catalytic (PTC) reactions to gain insight into steric control factors in such processes. Only very moderate e.e.s were observed. A SAMP hydrazone related catalyst (7a) reported by other authors was fully characterized. Racemic reaction products were obtained in two alkylations of diphenylmethylene benzylimine in the presence of this pure catalyst 7a. Very high e.e.s reported previously by others could not be reproduced. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2235 / 2244

页数：10

共 24 条

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