Highly enantioselective [3+2] annulation of cyclic enol silyl ethers with donor-acceptor cyclopropanes: Accessing 3a-hydroxy [n.3.0]carbobicycles

Hao Xu; Jian Ping Qu; Saihu Liao; Hu Xiong; Yong Tang

doi:10.1002/anie.201300032

Highly enantioselective [3+2] annulation of cyclic enol silyl ethers with donor-acceptor cyclopropanes: Accessing 3a-hydroxy [n.3.0]carbobicycles

Hao Xu, Jian Ping Qu, Saihu Liao, Hu Xiong, Yong Tang

CAS - Shanghai Institute of Organic Chemistry

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

122 Scopus citations

Abstract

A new fuse: The title reaction was realized using a new bisoxazoline (BOX)/Cu^II catalyst. This reaction works well with cyclic enol silyl ethers of different sizes, and can be extended to dienol and benzene-fused substrates, thus providing an effective and general access to a range of 3a-hydroxy [n.3.0]carbobicycles which are found as a core structure in many natural products. TBDPS=tert-butyldiphenylsilyl.

Original language	English
Pages (from-to)	4004-4007
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	14
DOIs	https://doi.org/10.1002/anie.201300032
State	Published - 2 Apr 2013
Externally published	Yes

Keywords

annulations
asymmetric catalysis
copper
fused-ring systems
small rings

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abstract = "A new fuse: The title reaction was realized using a new bisoxazoline (BOX)/CuII catalyst. This reaction works well with cyclic enol silyl ethers of different sizes, and can be extended to dienol and benzene-fused substrates, thus providing an effective and general access to a range of 3a-hydroxy [n.3.0]carbobicycles which are found as a core structure in many natural products. TBDPS=tert-butyldiphenylsilyl.",

keywords = "annulations, asymmetric catalysis, copper, fused-ring systems, small rings",

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T1 - Highly enantioselective [3+2] annulation of cyclic enol silyl ethers with donor-acceptor cyclopropanes

T2 - Accessing 3a-hydroxy [n.3.0]carbobicycles

AU - Xu, Hao

AU - Qu, Jian Ping

AU - Liao, Saihu

AU - Xiong, Hu

AU - Tang, Yong

PY - 2013/4/2

Y1 - 2013/4/2

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AB - A new fuse: The title reaction was realized using a new bisoxazoline (BOX)/CuII catalyst. This reaction works well with cyclic enol silyl ethers of different sizes, and can be extended to dienol and benzene-fused substrates, thus providing an effective and general access to a range of 3a-hydroxy [n.3.0]carbobicycles which are found as a core structure in many natural products. TBDPS=tert-butyldiphenylsilyl.

KW - annulations

KW - asymmetric catalysis

KW - copper

KW - fused-ring systems

KW - small rings

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M3 - 文章

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AN - SCOPUS:84875759358

SN - 1433-7851

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EP - 4007

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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ER -

Highly enantioselective [3+2] annulation of cyclic enol silyl ethers with donor-acceptor cyclopropanes: Accessing 3a-hydroxy [n.3.0]carbobicycles

Abstract

Keywords

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