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

Choong Eui Song; Chun Rim Oh; Eun Too Roh; Sang Gi Lee; Jung Hoon Choi

doi:10.1016/S0957-4166(99)00040-3

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

Choong Eui Song
, Chun Rim Oh
, Eun Too Roh
, Sang Gi Lee
, Jung Hoon Choi

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

27 Scopus citations

Abstract

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)₂PHAL as a chiral ligand. Simple recrystallization of crude product (containing regioisomer and diol) from ethyl acetate gave the enantiomerically pure product.

Original language	English
Pages (from-to)	671-674
Number of pages	4
Journal	Tetrahedron Asymmetry
Volume	10
Issue number	4
DOIs	https://doi.org/10.1016/S0957-4166(99)00040-3
State	Published - 26 Feb 1999

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title = "One-step synthesis of paclitaxel side-chain precursor: Benzamide-based asymmetric aminohydroxylation of isopropyl trans-cinnamate",

abstract = "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)2PHAL as a chiral ligand. Simple recrystallization of crude product (containing regioisomer and diol) from ethyl acetate gave the enantiomerically pure product.",

author = "Song, \{Choong Eui\} and Oh, \{Chun Rim\} and Roh, \{Eun Too\} and Lee, \{Sang Gi\} and Choi, \{Jung Hoon\}",

year = "1999",

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doi = "10.1016/S0957-4166(99)00040-3",

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T1 - One-step synthesis of paclitaxel side-chain precursor

T2 - Benzamide-based asymmetric aminohydroxylation of isopropyl trans-cinnamate

AU - Song, Choong Eui

AU - Oh, Chun Rim

AU - Roh, Eun Too

AU - Lee, Sang Gi

AU - Choi, Jung Hoon

PY - 1999/2/26

Y1 - 1999/2/26

N2 - 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)2PHAL as a chiral ligand. Simple recrystallization of crude product (containing regioisomer and diol) from ethyl acetate gave the enantiomerically pure product.

AB - 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)2PHAL as a chiral ligand. Simple recrystallization of crude product (containing regioisomer and diol) from ethyl acetate gave the enantiomerically pure product.

UR - https://www.scopus.com/pages/publications/0000715987

U2 - 10.1016/S0957-4166(99)00040-3

DO - 10.1016/S0957-4166(99)00040-3

M3 - Article

AN - SCOPUS:0000715987

SN - 0957-4166

VL - 10

SP - 671

EP - 674

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 4

ER -

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

Abstract

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