Chemoselective O-methylation of N-acylated/sulfonylated tyrosine derivatives

被引：11

作者：

Attolini, M ^{[1
]}

Boxus, T ^{[1
]}

Biltresse, S ^{[1
]}

Marchand-Brynaert, J ^{[1
]}

机构：

[1] Univ Catholique Louvain, Unite Chim Organ & Med, B-1348 Louvain, Belgium

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 07期

关键词：

D O I：

10.1016/S0040-4039(01)02349-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methyl ethers (6a and 6b) of N-trifluoroacetyl- and N-(m-trifluoromethyl) phenylsulfonyl-6-nitro-tyrosine t-butyl ester were readily prepared by modified Mitsunobu reaction (DPPE. DIAD, MeOH). Williamson (Mel, K2CO3 or LiCO3 or NaOH under phase transfer) and classical Mitsunobu conditions (PPh3, DEAD, MeOH) gave O,N-dimethylated derivatives (7a and 7b) as side or main products. O- versus N-selectivity in tyrosine methylation reactions depends on both pK(a) values and steric factors. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1187 / 1188

页数：2

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