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

^*此作品的通讯作者

化学与分子工程学院

East China Normal University
Central China Normal University
CAS - Shanghai Institute of Organic Chemistry

科研成果: 期刊稿件 › 文章 › 同行评审

95 引用（Scopus）

摘要

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.

源语言	英语
页（从-至）	8588-8593
页数	6
期刊	ACS Catalysis
卷	7
期	12
DOI	https://doi.org/10.1021/acscatal.7b03370
出版状态	已出版 - 1 12月 2017

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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",

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TY - JOUR

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