Utilization of CO2 as a C1 Building Block in a Tandem Asymmetric A3 Coupling-Carboxylative Cyclization Sequence to 2-Oxazolidinones

Xiao Tong Gao; Chen Chen Gan; Si Yue Liu; Feng Zhou; Hai Hong Wu; Jian Zhou

doi:10.1021/acscatal.7b03370

Utilization of CO₂ as a C1 Building Block in a Tandem Asymmetric A³ Coupling-Carboxylative Cyclization Sequence to 2-Oxazolidinones

Xiao Tong Gao
, Chen Chen Gan
, Si Yue Liu
, Feng Zhou^*
, Hai Hong Wu
, Jian Zhou

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

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

93 Scopus citations

Abstract

We report a tandem asymmetric aldehyde-alkyne-amine (A³) coupling-carboxylative cyclization sequence for the highly enantioselective synthesis of chiral N-aryl 2-oxazolidinones. This is a rare example of a multicatalyst-promoted asymmetric tandem reaction using CO₂ as a C1 synthon. Notably, the copper species and ligand from the upstream A³ reaction are internally reused to facilitate the downstream silver-catalyzed carboxylative cyclization.

Original language	English
Pages (from-to)	8588-8593
Number of pages	6
Journal	ACS Catalysis
Volume	7
Issue number	12
DOIs	https://doi.org/10.1021/acscatal.7b03370
State	Published - 1 Dec 2017

Keywords

2-oxazolidinone
A coupling
CO transformation
asymmetric tandem reaction
carboxylative cyclization

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10.1021/acscatal.7b03370

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title = "Utilization of CO2 as a C1 Building Block in a Tandem Asymmetric A3 Coupling-Carboxylative Cyclization Sequence to 2-Oxazolidinones",

abstract = "We report a tandem asymmetric aldehyde-alkyne-amine (A3) coupling-carboxylative cyclization sequence for the highly enantioselective synthesis of chiral N-aryl 2-oxazolidinones. This is a rare example of a multicatalyst-promoted asymmetric tandem reaction using CO2 as a C1 synthon. Notably, the copper species and ligand from the upstream A3 reaction are internally reused to facilitate the downstream silver-catalyzed carboxylative cyclization.",

keywords = "2-oxazolidinone, A coupling, CO transformation, asymmetric tandem reaction, carboxylative cyclization",

author = "Gao, \{Xiao Tong\} and Gan, \{Chen Chen\} and Liu, \{Si Yue\} and Feng Zhou and Wu, \{Hai Hong\} and Jian Zhou",

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

year = "2017",

month = dec,

day = "1",

doi = "10.1021/acscatal.7b03370",

language = "英语",

volume = "7",

pages = "8588--8593",

journal = "ACS Catalysis",

issn = "2155-5435",

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T1 - Utilization of CO2 as a C1 Building Block in a Tandem Asymmetric A3 Coupling-Carboxylative Cyclization Sequence to 2-Oxazolidinones

AU - Gao, Xiao Tong

AU - Gan, Chen Chen

AU - Liu, Si Yue

AU - Zhou, Feng

AU - Wu, Hai Hong

AU - Zhou, Jian

PY - 2017/12/1

Y1 - 2017/12/1

N2 - We report a tandem asymmetric aldehyde-alkyne-amine (A3) coupling-carboxylative cyclization sequence for the highly enantioselective synthesis of chiral N-aryl 2-oxazolidinones. This is a rare example of a multicatalyst-promoted asymmetric tandem reaction using CO2 as a C1 synthon. Notably, the copper species and ligand from the upstream A3 reaction are internally reused to facilitate the downstream silver-catalyzed carboxylative cyclization.

AB - We report a tandem asymmetric aldehyde-alkyne-amine (A3) coupling-carboxylative cyclization sequence for the highly enantioselective synthesis of chiral N-aryl 2-oxazolidinones. This is a rare example of a multicatalyst-promoted asymmetric tandem reaction using CO2 as a C1 synthon. Notably, the copper species and ligand from the upstream A3 reaction are internally reused to facilitate the downstream silver-catalyzed carboxylative cyclization.

KW - 2-oxazolidinone

KW - A coupling

KW - CO transformation

KW - asymmetric tandem reaction

KW - carboxylative cyclization

UR - https://www.scopus.com/pages/publications/85036632756

U2 - 10.1021/acscatal.7b03370

DO - 10.1021/acscatal.7b03370

M3 - 文章

AN - SCOPUS:85036632756

SN - 2155-5435

VL - 7

SP - 8588

EP - 8593

JO - ACS Catalysis

JF - ACS Catalysis

IS - 12

ER -

Utilization of CO₂ as a C1 Building Block in a Tandem Asymmetric A³ Coupling-Carboxylative Cyclization Sequence to 2-Oxazolidinones

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Keywords

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