Catalytic Enantioselective Cyclopropenation of Internal Alkynes: Access to Difluoromethylated Three-Membered Carbocycles: Access to Difluoromethylated Three-Membered Carbocycles

Zhi-Qi Zhang; Meng-Meng Zheng; Xiao-Song Xue; Ilan Marek; Fa-Guang Zhang; Jun-An Ma

doi:10.1002/anie.201911701

Catalytic Enantioselective Cyclopropenation of Internal Alkynes: Access to Difluoromethylated Three-Membered Carbocycles: Access to Difluoromethylated Three-Membered Carbocycles

Zhi-Qi Zhang
, Meng-Meng Zheng
, Xiao-Song Xue
, Ilan Marek
, Fa-Guang Zhang
, Jun-An Ma

Technion - Israel Institute of Technology

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

Abstract

Herein we described an efficient Rh^II-catalyzed enantioselective cyclopropenation reaction of internal alkynes with a masked difluorodiazoethane reagent (PhSO₂CF₂CHN₂, Ps-DFA). This asymmetric transformation offers efficient access to a broad range of enantioenriched difluoromethylated cyclopropenes (40 examples, up to 99 % yield, 97 % ee). The synthetic utility of obtained strained carbocycles is demonstrated by subsequent stereodefined processes, including cross-couplings, hydrogenation, Diels–Alder reaction, and Pauson–Khand reaction.

Original language	English GB
Pages (from-to)	18191-18196
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	58
Issue number	50
DOIs	https://doi.org/10.1002/anie.201911701
State	Published - 11 Nov 2019

Keywords

cyclopropenation
diazo compounds
homogeneous catalysis
internal alkynes
metal carbenes

ASJC Scopus subject areas

Catalysis
General Chemistry

Access to Document

10.1002/anie.201911701

Cite this

@article{515b80274d4645589f37c06acb9908c8,

title = "Catalytic Enantioselective Cyclopropenation of Internal Alkynes: Access to Difluoromethylated Three-Membered Carbocycles: Access to Difluoromethylated Three-Membered Carbocycles",

abstract = "Herein we described an efficient RhII-catalyzed enantioselective cyclopropenation reaction of internal alkynes with a masked difluorodiazoethane reagent (PhSO2CF2CHN2, Ps-DFA). This asymmetric transformation offers efficient access to a broad range of enantioenriched difluoromethylated cyclopropenes (40 examples, up to 99 \% yield, 97 \% ee). The synthetic utility of obtained strained carbocycles is demonstrated by subsequent stereodefined processes, including cross-couplings, hydrogenation, Diels{\textendash}Alder reaction, and Pauson{\textendash}Khand reaction.",

keywords = "cyclopropenation, diazo compounds, homogeneous catalysis, internal alkynes, metal carbenes",

author = "Zhi-Qi Zhang and Meng-Meng Zheng and Xiao-Song Xue and Ilan Marek and Fa-Guang Zhang and Jun-An Ma",

note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2019",

month = nov,

day = "11",

doi = "10.1002/anie.201911701",

language = "الإنجليزيّة",

volume = "58",

pages = "18191--18196",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "50",

}

Catalytic Enantioselective Cyclopropenation of Internal Alkynes: Access to Difluoromethylated Three-Membered Carbocycles: Access to Difluoromethylated Three-Membered Carbocycles. / Zhang, Zhi-Qi; Zheng, Meng-Meng; Xue, Xiao-Song et al.
In: Angewandte Chemie - International Edition, Vol. 58, No. 50, 11.11.2019, p. 18191-18196.

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

TY - JOUR

T1 - Catalytic Enantioselective Cyclopropenation of Internal Alkynes: Access to Difluoromethylated Three-Membered Carbocycles

T2 - Access to Difluoromethylated Three-Membered Carbocycles

AU - Zhang, Zhi-Qi

AU - Zheng, Meng-Meng

AU - Xue, Xiao-Song

AU - Marek, Ilan

AU - Zhang, Fa-Guang

AU - Ma, Jun-An

PY - 2019/11/11

Y1 - 2019/11/11

N2 - Herein we described an efficient RhII-catalyzed enantioselective cyclopropenation reaction of internal alkynes with a masked difluorodiazoethane reagent (PhSO2CF2CHN2, Ps-DFA). This asymmetric transformation offers efficient access to a broad range of enantioenriched difluoromethylated cyclopropenes (40 examples, up to 99 % yield, 97 % ee). The synthetic utility of obtained strained carbocycles is demonstrated by subsequent stereodefined processes, including cross-couplings, hydrogenation, Diels–Alder reaction, and Pauson–Khand reaction.

AB - Herein we described an efficient RhII-catalyzed enantioselective cyclopropenation reaction of internal alkynes with a masked difluorodiazoethane reagent (PhSO2CF2CHN2, Ps-DFA). This asymmetric transformation offers efficient access to a broad range of enantioenriched difluoromethylated cyclopropenes (40 examples, up to 99 % yield, 97 % ee). The synthetic utility of obtained strained carbocycles is demonstrated by subsequent stereodefined processes, including cross-couplings, hydrogenation, Diels–Alder reaction, and Pauson–Khand reaction.

KW - cyclopropenation

KW - diazo compounds

KW - homogeneous catalysis

KW - internal alkynes

KW - metal carbenes

UR - https://www.scopus.com/pages/publications/85075184184

U2 - 10.1002/anie.201911701

DO - 10.1002/anie.201911701

M3 - مقالة

SN - 1433-7851

VL - 58

SP - 18191

EP - 18196

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 50

ER -

Catalytic Enantioselective Cyclopropenation of Internal Alkynes: Access to Difluoromethylated Three-Membered Carbocycles: Access to Difluoromethylated Three-Membered Carbocycles

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this