Iridium-catalyzed asymmetric hydrogenation of α-substituted α,β-unsaturated acyclic ketones: Enantioselective total synthesis of (-)-mesembrine

Qian Qian Zhang; Jian Hua Xie; Xiao Hui Yang; Jian Bo Xie; Qi Lin Zhou

doi:10.1021/ol302842h

Iridium-catalyzed asymmetric hydrogenation of α-substituted α,β-unsaturated acyclic ketones: Enantioselective total synthesis of (-)-mesembrine

Qian Qian Zhang
, Jian Hua Xie^*
, Xiao Hui Yang
, Jian Bo Xie
, Qi Lin Zhou

^*Corresponding author for this work

Nankai University

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

69 Citations (Scopus)

Abstract

A highly efficient asymmetric hydrogenation of α-substituted α,β-unsaturated acyclic ketones catalyzed by chiral spiro iridium complexes for the preparation of chiral 2-substituted allylic alcohols has been developed (ee up to 99.7%). This method provides a concise route to (-)-mesembrine (34% yield, 12 steps).

Original language	English
Pages (from-to)	6158-6161
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	24
DOIs	https://doi.org/10.1021/ol302842h
Publication status	Published - 21 Dec 2012
Externally published	Yes

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10.1021/ol302842h

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title = "Iridium-catalyzed asymmetric hydrogenation of α-substituted α,β-unsaturated acyclic ketones: Enantioselective total synthesis of (-)-mesembrine",

abstract = "A highly efficient asymmetric hydrogenation of α-substituted α,β-unsaturated acyclic ketones catalyzed by chiral spiro iridium complexes for the preparation of chiral 2-substituted allylic alcohols has been developed (ee up to 99.7\%). This method provides a concise route to (-)-mesembrine (34\% yield, 12 steps).",

author = "Zhang, \{Qian Qian\} and Xie, \{Jian Hua\} and Yang, \{Xiao Hui\} and Xie, \{Jian Bo\} and Zhou, \{Qi Lin\}",

year = "2012",

month = dec,

day = "21",

doi = "10.1021/ol302842h",

language = "English",

volume = "14",

pages = "6158--6161",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "24",

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T1 - Iridium-catalyzed asymmetric hydrogenation of α-substituted α,β-unsaturated acyclic ketones

T2 - Enantioselective total synthesis of (-)-mesembrine

AU - Zhang, Qian Qian

AU - Xie, Jian Hua

AU - Yang, Xiao Hui

AU - Xie, Jian Bo

AU - Zhou, Qi Lin

PY - 2012/12/21

Y1 - 2012/12/21

N2 - A highly efficient asymmetric hydrogenation of α-substituted α,β-unsaturated acyclic ketones catalyzed by chiral spiro iridium complexes for the preparation of chiral 2-substituted allylic alcohols has been developed (ee up to 99.7%). This method provides a concise route to (-)-mesembrine (34% yield, 12 steps).

AB - A highly efficient asymmetric hydrogenation of α-substituted α,β-unsaturated acyclic ketones catalyzed by chiral spiro iridium complexes for the preparation of chiral 2-substituted allylic alcohols has been developed (ee up to 99.7%). This method provides a concise route to (-)-mesembrine (34% yield, 12 steps).

UR - https://www.scopus.com/pages/publications/84871545837

U2 - 10.1021/ol302842h

DO - 10.1021/ol302842h

M3 - Article

C2 - 23210605

AN - SCOPUS:84871545837

SN - 1523-7060

VL - 14

SP - 6158

EP - 6161

JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

Iridium-catalyzed asymmetric hydrogenation of α-substituted α,β-unsaturated acyclic ketones: Enantioselective total synthesis of (-)-mesembrine

Abstract

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