Enantioselective synthesis of (S)-α-methylphenylalanine using (S)-BINOLAMs as new phase-transfer catalysts

被引：40

作者：

Casas, J

Nájera, C

Sansano, JM

González, J

Saá, JM

Vega, M

机构：

[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, Alicante 03080, Spain

[2] Univ Illes Balears, Dept Quim, E-07071 Palma de Mallorca, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 05期

关键词：

D O I：

10.1016/S0957-4166(01)00107-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A series of (S)-bis(aminomethyl)binaphthols [(S)-BINOLAMs] 4 have been prepared and used as catalysts in the enantioselective C-alkylation reaction of the aldimine Schiff bases of alanine esters 5 under solid-liquid phase-transfer catalysis (PTC) conditions employing NaOH as base in toluene at room temperature. (S)-3.3'-Bis[(diethylamino)methyl]2.2'-dihydroxy 1,1-binaphthalene 4a gave the best e.e.s. (S)-alpha -Methylphenylalanine 7 was isolated, after hydrolysis of the iminoester, in 85% yield with an e.e. of 68%. (C) 2001 Elsevier Science Ltd. All rights reserved.

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页码：699 / 702

页数：4

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