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

Authors
Song, CE Oh, CR Roh, EJ Lee, SG Choi, JH
Citation
Ce. Song et al., One-step synthesis of paclitaxel side-chain precursor: benzamide-based asymmetric aminohydroxylation of isopropyl trans-cinnamate, TETRAHEDR-A, 10(4), 1999, pp. 671-674
Citations number
4
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
4
Year of publication
1999
Pages
671 - 674
Database
ISI
SICI code
0957-4166(19990226)10:4<671:OSOPSP>2.0.ZU;2-L
Abstract
A highly enantioselective (up to 97% ee) one-step synthesis of paclitaxel s ide chain precursor, (2R,3S)-isopropyl 3-benzamido-2-hydroxy-3-phenylpropio nate has been achieved by osmium-catalyzed asymmetric aminohydroxylation of isopropyl trans-cinnamate with N-bromobenzamide as an oxidant/nitrogen sou rce in the presence of (DHQ)(2)PHAL as a chiral ligand. Simple recrystalliz ation of crude product (containing regioisomer and diol) from ethyl acetate gave the enantiomerically pure product. (C) 1999 Elsevier Science Ltd. All rights reserved.