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

^*此作品的通讯作者

Nankai University

科研成果: 期刊稿件 › 文章 › 同行评审

69 引用（Scopus）

摘要

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).

源语言	英语
页（从-至）	6158-6161
页数	4
期刊	Organic Letters
卷	14
期	24
DOI	https://doi.org/10.1021/ol302842h
出版状态	已出版 - 21 12月 2012
已对外发布	是

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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",

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day = "21",

doi = "10.1021/ol302842h",

language = "English",

volume = "14",

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journal = "Organic Letters",

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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

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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

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