Enantioselective Phosphine-Catalyzed Allylic Alkylations of mix-Indene with MBH Carbonates

Junyou Zhang; Hai Hong Wu; Junliang Zhang

doi:10.1021/acs.orglett.7b02895

Enantioselective Phosphine-Catalyzed Allylic Alkylations of mix-Indene with MBH Carbonates

Junyou Zhang
, Hai Hong Wu^*
, Junliang Zhang

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

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

53 Scopus citations

Abstract

The first enantioenriched synthesis of 1,1,3-trisubstituted (trifluoromethyl)indene derivatives, bearing a quaternary stereogenic carbon center, is reported using a simple chiral sulfinamide phosphine-catalyzed asymmetric allylic alkylation of a mixture of indenes with Morita-Baylis-Hillman carbonates. The resulting derivatives can serve as a valuable synthetic building block for some drugs and natural products. Broad substrate scope and high regio- and enantioselectivity of this reaction were particularly remarkable.

Original language	English
Pages (from-to)	6080-6083
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	22
DOIs	https://doi.org/10.1021/acs.orglett.7b02895
State	Published - 17 Nov 2017

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title = "Enantioselective Phosphine-Catalyzed Allylic Alkylations of mix-Indene with MBH Carbonates",

abstract = "The first enantioenriched synthesis of 1,1,3-trisubstituted (trifluoromethyl)indene derivatives, bearing a quaternary stereogenic carbon center, is reported using a simple chiral sulfinamide phosphine-catalyzed asymmetric allylic alkylation of a mixture of indenes with Morita-Baylis-Hillman carbonates. The resulting derivatives can serve as a valuable synthetic building block for some drugs and natural products. Broad substrate scope and high regio- and enantioselectivity of this reaction were particularly remarkable.",

author = "Junyou Zhang and Wu, \{Hai Hong\} and Junliang Zhang",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

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doi = "10.1021/acs.orglett.7b02895",

language = "英语",

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journal = "Organic Letters",

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T1 - Enantioselective Phosphine-Catalyzed Allylic Alkylations of mix-Indene with MBH Carbonates

AU - Zhang, Junyou

AU - Wu, Hai Hong

AU - Zhang, Junliang

PY - 2017/11/17

Y1 - 2017/11/17

N2 - The first enantioenriched synthesis of 1,1,3-trisubstituted (trifluoromethyl)indene derivatives, bearing a quaternary stereogenic carbon center, is reported using a simple chiral sulfinamide phosphine-catalyzed asymmetric allylic alkylation of a mixture of indenes with Morita-Baylis-Hillman carbonates. The resulting derivatives can serve as a valuable synthetic building block for some drugs and natural products. Broad substrate scope and high regio- and enantioselectivity of this reaction were particularly remarkable.

AB - The first enantioenriched synthesis of 1,1,3-trisubstituted (trifluoromethyl)indene derivatives, bearing a quaternary stereogenic carbon center, is reported using a simple chiral sulfinamide phosphine-catalyzed asymmetric allylic alkylation of a mixture of indenes with Morita-Baylis-Hillman carbonates. The resulting derivatives can serve as a valuable synthetic building block for some drugs and natural products. Broad substrate scope and high regio- and enantioselectivity of this reaction were particularly remarkable.

UR - https://www.scopus.com/pages/publications/85034646828

U2 - 10.1021/acs.orglett.7b02895

DO - 10.1021/acs.orglett.7b02895

M3 - 文章

C2 - 29077416

AN - SCOPUS:85034646828

SN - 1523-7060

VL - 19

SP - 6080

EP - 6083

JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

Enantioselective Phosphine-Catalyzed Allylic Alkylations of mix-Indene with MBH Carbonates

Abstract

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