Catalytic asymmetric construction of spiro(γ-butyrolactam-γ- butyrolactone) moieties through sequential reactions of cyclic imino esters with Morita-Baylis-Hillman bromides

Huai Long Teng; He Huang; Chun Jiang Wang

doi:10.1002/chem.201201475

Catalytic asymmetric construction of spiro(γ-butyrolactam-γ- butyrolactone) moieties through sequential reactions of cyclic imino esters with Morita-Baylis-Hillman bromides

Huai Long Teng
, He Huang
, Chun Jiang Wang^*

^*此作品的通讯作者

Wuhan University
Nankai University

科研成果: 期刊稿件 › 文章 › 同行评审

46 引用（Scopus）

摘要

Spiro(γ-butyrolactam-γ-butyrolactone): A route to enantioenriched spiro(γ-butyrolactam-γ-butyrolactone) compounds, a valuable motif for drug discovery, was developed by use of a highly efficient copper(I)/TF-BiphamPhos-catalyzed tandem Michael addition-elimination of homoserine lactone derived cyclic imino esters with Morita-Baylis-Hillman (MBH) bromides, followed by treatment with para-toluenesulfonic acid (see scheme).

源语言	英语
页（从-至）	12614-12618
页数	5
期刊	Chemistry - A European Journal
卷	18
期	40
DOI	https://doi.org/10.1002/chem.201201475
出版状态	已出版 - 1 10月 2012
已对外发布	是

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title = "Catalytic asymmetric construction of spiro(γ-butyrolactam-γ- butyrolactone) moieties through sequential reactions of cyclic imino esters with Morita-Baylis-Hillman bromides",

abstract = "Spiro(γ-butyrolactam-γ-butyrolactone): A route to enantioenriched spiro(γ-butyrolactam-γ-butyrolactone) compounds, a valuable motif for drug discovery, was developed by use of a highly efficient copper(I)/TF-BiphamPhos-catalyzed tandem Michael addition-elimination of homoserine lactone derived cyclic imino esters with Morita-Baylis-Hillman (MBH) bromides, followed by treatment with para-toluenesulfonic acid (see scheme).",

keywords = "asymmetric catalysis, bromides, diastereoselectivity, enantioselectivity, imino esters, spiro compounds",

author = "Teng, \{Huai Long\} and He Huang and Wang, \{Chun Jiang\}",

year = "2012",

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doi = "10.1002/chem.201201475",

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AU - Teng, Huai Long

AU - Huang, He

AU - Wang, Chun Jiang

PY - 2012/10/1

Y1 - 2012/10/1

N2 - Spiro(γ-butyrolactam-γ-butyrolactone): A route to enantioenriched spiro(γ-butyrolactam-γ-butyrolactone) compounds, a valuable motif for drug discovery, was developed by use of a highly efficient copper(I)/TF-BiphamPhos-catalyzed tandem Michael addition-elimination of homoserine lactone derived cyclic imino esters with Morita-Baylis-Hillman (MBH) bromides, followed by treatment with para-toluenesulfonic acid (see scheme).

AB - Spiro(γ-butyrolactam-γ-butyrolactone): A route to enantioenriched spiro(γ-butyrolactam-γ-butyrolactone) compounds, a valuable motif for drug discovery, was developed by use of a highly efficient copper(I)/TF-BiphamPhos-catalyzed tandem Michael addition-elimination of homoserine lactone derived cyclic imino esters with Morita-Baylis-Hillman (MBH) bromides, followed by treatment with para-toluenesulfonic acid (see scheme).

KW - asymmetric catalysis

KW - bromides

KW - diastereoselectivity

KW - enantioselectivity

KW - imino esters

KW - spiro compounds

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VL - 18

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JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 40

ER -

Catalytic asymmetric construction of spiro(γ-butyrolactam-γ- butyrolactone) moieties through sequential reactions of cyclic imino esters with Morita-Baylis-Hillman bromides

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