Highly diastereoselective construction of fused carbocycles from cyclopropane-1,1-dicarboxylates and cyclic enol silyl ethers: Scope, Mechanism, and origin of diastereoselectivity

Jian Ping Qu; Yong Liang; Hao Xu; Xiu Li Sun; Zhi Xiang Yu; Yong Tang

doi:10.1002/chem.201103495

Highly diastereoselective construction of fused carbocycles from cyclopropane-1,1-dicarboxylates and cyclic enol silyl ethers: Scope, Mechanism, and origin of diastereoselectivity

Jian Ping Qu, Yong Liang, Hao Xu, Xiu Li Sun, Zhi Xiang Yu, Yong Tang

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

71 Scopus citations

Abstract

Cyclopropane rings true: By selecting the appropriate substituents on the ester and silyl groups, fused cyclopentane derivatives with multiple contiguous stereocenters can be synthesized with excellent diastereoselectivity through Cu ^II/bisoxazoline-catalyzed intermolecular [3+2] cycloaddition reactions of cyclopropane-1,1-dicarboxylates and cyclic enol silyl ethers (see scheme).

Original language	English
Pages (from-to)	2196-2201
Number of pages	6
Journal	Chemistry - A European Journal
Volume	18
Issue number	8
DOIs	https://doi.org/10.1002/chem.201103495
State	Published - 20 Feb 2012
Externally published	Yes

Keywords

cycloaddition
cyclopropane
density functional calculations
diastereoselectivity
reaction mechanisms

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10.1002/chem.201103495

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title = "Highly diastereoselective construction of fused carbocycles from cyclopropane-1,1-dicarboxylates and cyclic enol silyl ethers: Scope, Mechanism, and origin of diastereoselectivity",

abstract = "Cyclopropane rings true: By selecting the appropriate substituents on the ester and silyl groups, fused cyclopentane derivatives with multiple contiguous stereocenters can be synthesized with excellent diastereoselectivity through Cu II/bisoxazoline-catalyzed intermolecular [3+2] cycloaddition reactions of cyclopropane-1,1-dicarboxylates and cyclic enol silyl ethers (see scheme).",

keywords = "cycloaddition, cyclopropane, density functional calculations, diastereoselectivity, reaction mechanisms",

author = "Qu, {Jian Ping} and Yong Liang and Hao Xu and Sun, {Xiu Li} and Yu, {Zhi Xiang} and Yong Tang",

year = "2012",

month = feb,

day = "20",

doi = "10.1002/chem.201103495",

language = "英语",

volume = "18",

pages = "2196--2201",

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publisher = "John Wiley and Sons Inc",

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}

Highly diastereoselective construction of fused carbocycles from cyclopropane-1,1-dicarboxylates and cyclic enol silyl ethers: Scope, Mechanism, and origin of diastereoselectivity. / Qu, Jian Ping; Liang, Yong; Xu, Hao et al.
In: Chemistry - A European Journal, Vol. 18, No. 8, 20.02.2012, p. 2196-2201.

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

TY - JOUR

T1 - Highly diastereoselective construction of fused carbocycles from cyclopropane-1,1-dicarboxylates and cyclic enol silyl ethers

T2 - Scope, Mechanism, and origin of diastereoselectivity

AU - Qu, Jian Ping

AU - Liang, Yong

AU - Xu, Hao

AU - Sun, Xiu Li

AU - Yu, Zhi Xiang

AU - Tang, Yong

PY - 2012/2/20

Y1 - 2012/2/20

N2 - Cyclopropane rings true: By selecting the appropriate substituents on the ester and silyl groups, fused cyclopentane derivatives with multiple contiguous stereocenters can be synthesized with excellent diastereoselectivity through Cu II/bisoxazoline-catalyzed intermolecular [3+2] cycloaddition reactions of cyclopropane-1,1-dicarboxylates and cyclic enol silyl ethers (see scheme).

AB - Cyclopropane rings true: By selecting the appropriate substituents on the ester and silyl groups, fused cyclopentane derivatives with multiple contiguous stereocenters can be synthesized with excellent diastereoselectivity through Cu II/bisoxazoline-catalyzed intermolecular [3+2] cycloaddition reactions of cyclopropane-1,1-dicarboxylates and cyclic enol silyl ethers (see scheme).

KW - cycloaddition

KW - cyclopropane

KW - density functional calculations

KW - diastereoselectivity

KW - reaction mechanisms

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U2 - 10.1002/chem.201103495

DO - 10.1002/chem.201103495

M3 - 文章

C2 - 22262651

AN - SCOPUS:84863157939

SN - 0947-6539

VL - 18

SP - 2196

EP - 2201

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 8

ER -

Highly diastereoselective construction of fused carbocycles from cyclopropane-1,1-dicarboxylates and cyclic enol silyl ethers: Scope, Mechanism, and origin of diastereoselectivity

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Keywords

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