One-step synthesis of paclitaxel side-chain precursor:: benzamide-based asymmetric aminohydroxylation of isopropyl trans-cinnamate

被引：19

作者：

Song, CE

Oh, CR

Roh, EJ

Lee, SG

Choi, JH

机构：

[1] Korea Inst Sci & Technol, Div Appl Sci, Seoul 130650, South Korea

[2] Hanyang Univ, Dept Chem, Seoul 133791, South Korea

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 04期

关键词：

D O I：

10.1016/S0957-4166(99)00040-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A highly enantioselective (up to 97% ee) one-step synthesis of paclitaxel side chain precursor, (2R,3S)-isopropyl 3-benzamido-2-hydroxy-3-phenylpropionate has been achieved by osmium-catalyzed asymmetric aminohydroxylation of isopropyl trans-cinnamate with N-bromobenzamide as an oxidant/nitrogen source in the presence of (DHQ)(2)PHAL as a chiral ligand. Simple recrystallization of crude product (containing regioisomer and diol) from ethyl acetate gave the enantiomerically pure product. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：671 / 674

页数：4

共 4 条

[1] The removal of HX from organic compounds by means of bases III The rates of removal of hydrogen bromide from substituted N-bromobenzamides and their relative ease of rearrangement in the presence of alkali - The Hofmann rearrangement [J].