Rhodium-Catalyzed Branched and Enantioselective Direct α-Allylic Alkylation of Simple Ketones with Alkynes

Liyu Xie; Haijian Yang; Mingliang Ma; Dong Xing

doi:10.1021/acs.orglett.0c00375

Rhodium-Catalyzed Branched and Enantioselective Direct α-Allylic Alkylation of Simple Ketones with Alkynes

Liyu Xie
, Haijian Yang
, Mingliang Ma
, Dong Xing^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

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

13 Scopus citations

Abstract

Herein, we report the first direct branched-selective α-allylic alkylation of simple ketones with alkynes under rhodium and secondary amine cooperative catalysis. Through a rhodium-hydride-catalyzed allylic substitution pathway, a series of valuable Î,Î-unsaturated ketones are obtained with excellent regioselectivity in an atom-economic and byproduct-free manner. With a chiral BIPHEP ligand, high enantioselectivity has been achieved for this transformation.

Original language	English
Pages (from-to)	2007-2011
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.0c00375
State	Published - 6 Mar 2020

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title = "Rhodium-Catalyzed Branched and Enantioselective Direct α-Allylic Alkylation of Simple Ketones with Alkynes",

abstract = "Herein, we report the first direct branched-selective α-allylic alkylation of simple ketones with alkynes under rhodium and secondary amine cooperative catalysis. Through a rhodium-hydride-catalyzed allylic substitution pathway, a series of valuable {\^I},{\^I}-unsaturated ketones are obtained with excellent regioselectivity in an atom-economic and byproduct-free manner. With a chiral BIPHEP ligand, high enantioselectivity has been achieved for this transformation.",

author = "Liyu Xie and Haijian Yang and Mingliang Ma and Dong Xing",

note = "Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = mar,

day = "6",

doi = "10.1021/acs.orglett.0c00375",

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T1 - Rhodium-Catalyzed Branched and Enantioselective Direct α-Allylic Alkylation of Simple Ketones with Alkynes

AU - Xie, Liyu

AU - Yang, Haijian

AU - Ma, Mingliang

AU - Xing, Dong

PY - 2020/3/6

Y1 - 2020/3/6

N2 - Herein, we report the first direct branched-selective α-allylic alkylation of simple ketones with alkynes under rhodium and secondary amine cooperative catalysis. Through a rhodium-hydride-catalyzed allylic substitution pathway, a series of valuable Î,Î-unsaturated ketones are obtained with excellent regioselectivity in an atom-economic and byproduct-free manner. With a chiral BIPHEP ligand, high enantioselectivity has been achieved for this transformation.

AB - Herein, we report the first direct branched-selective α-allylic alkylation of simple ketones with alkynes under rhodium and secondary amine cooperative catalysis. Through a rhodium-hydride-catalyzed allylic substitution pathway, a series of valuable Î,Î-unsaturated ketones are obtained with excellent regioselectivity in an atom-economic and byproduct-free manner. With a chiral BIPHEP ligand, high enantioselectivity has been achieved for this transformation.

UR - https://www.scopus.com/pages/publications/85080876187

U2 - 10.1021/acs.orglett.0c00375

DO - 10.1021/acs.orglett.0c00375

M3 - 文章

C2 - 32065530

AN - SCOPUS:85080876187

SN - 1523-7060

VL - 22

SP - 2007

EP - 2011

JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

Rhodium-Catalyzed Branched and Enantioselective Direct α-Allylic Alkylation of Simple Ketones with Alkynes

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