Direct Activation of β-sp3-Carbons of Saturated Carboxylic Esters as Electrophilic Carbons via Oxidative Carbene Catalysis

Bin Liu; Weihong Wang; Ruoyan Huang; Jiekuan Yan; Jichang Wu; Wei Xue; Song Yang; Zhichao Jin; Yonggui Robin Chi

doi:10.1021/acs.orglett.7b03650

Direct Activation of β-sp³-Carbons of Saturated Carboxylic Esters as Electrophilic Carbons via Oxidative Carbene Catalysis

Bin Liu, Weihong Wang, Ruoyan Huang, Jiekuan Yan, Jichang Wu, Wei Xue, Song Yang^*, Zhichao Jin, Yonggui Robin Chi

^*Corresponding author for this work

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

37 Citations (Scopus)

Abstract

An N-heterocyclic carbene-catalyzed oxidative LUMO activation of the β-cabons of saturated carboxylic esters is disclosed. This approach allows for efficient asymmetric access to lactams and lactones by directly installing functional groups to the typically inert β-sp³ carbons of saturated esters. The use of HOBt as an additive was found to significantly improve both yields and enantioselectivities of the reactions.

Original language	English
Pages (from-to)	260-263
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	1
DOIs	https://doi.org/10.1021/acs.orglett.7b03650
Publication status	Published - Jan 5 2018
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2017 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.7b03650

Cite this

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title = "Direct Activation of β-sp3-Carbons of Saturated Carboxylic Esters as Electrophilic Carbons via Oxidative Carbene Catalysis",

abstract = "An N-heterocyclic carbene-catalyzed oxidative LUMO activation of the β-cabons of saturated carboxylic esters is disclosed. This approach allows for efficient asymmetric access to lactams and lactones by directly installing functional groups to the typically inert β-sp3 carbons of saturated esters. The use of HOBt as an additive was found to significantly improve both yields and enantioselectivities of the reactions.",

author = "Bin Liu and Weihong Wang and Ruoyan Huang and Jiekuan Yan and Jichang Wu and Wei Xue and Song Yang and Zhichao Jin and Chi, {Yonggui Robin}",

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doi = "10.1021/acs.orglett.7b03650",

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T1 - Direct Activation of β-sp3-Carbons of Saturated Carboxylic Esters as Electrophilic Carbons via Oxidative Carbene Catalysis

AU - Liu, Bin

AU - Wang, Weihong

AU - Huang, Ruoyan

AU - Yan, Jiekuan

AU - Wu, Jichang

AU - Xue, Wei

AU - Yang, Song

AU - Jin, Zhichao

AU - Chi, Yonggui Robin

PY - 2018/1/5

Y1 - 2018/1/5

N2 - An N-heterocyclic carbene-catalyzed oxidative LUMO activation of the β-cabons of saturated carboxylic esters is disclosed. This approach allows for efficient asymmetric access to lactams and lactones by directly installing functional groups to the typically inert β-sp3 carbons of saturated esters. The use of HOBt as an additive was found to significantly improve both yields and enantioselectivities of the reactions.

AB - An N-heterocyclic carbene-catalyzed oxidative LUMO activation of the β-cabons of saturated carboxylic esters is disclosed. This approach allows for efficient asymmetric access to lactams and lactones by directly installing functional groups to the typically inert β-sp3 carbons of saturated esters. The use of HOBt as an additive was found to significantly improve both yields and enantioselectivities of the reactions.

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