Merging of Palladium and Organocatalysis Enabled Asymmetric Decarboxylative (2+1) Cycloadditions toward Cyclopropanes

Biwei Yan; Pengchen Ma; Xiao Shu; Wenhao Yin; Wusheng Guo

doi:10.1021/acs.orglett.4c01088

Merging of Palladium and Organocatalysis Enabled Asymmetric Decarboxylative (2+1) Cycloadditions toward Cyclopropanes

Biwei Yan
, Pengchen Ma
, Xiao Shu
, Wenhao Yin
, Wusheng Guo

Frontier Institute of Science and Technology

Xi'an Jiaotong University

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

5 Scopus citations

Abstract

A cascade reaction enabling enantio- and diastereoselective construction of strained cyclopropanes is described. This asymmetric (2+1) annulation process uses vinyl methylene carbonate and 2-cyanoacrylate as reaction partners in the presence of Pd(PPh₃)₄ as a precatalyst and an enantioenriched phosphoramidite ligand featuring a morpholine functionality. Mechanistic investigations unveil that the PPh₃ derived from the Pd(PPh₃)₄ and the morpholine-containing phosphoramidite work as cooperative phosphorus and Brønsted base catalysts to promote the reaction.

Original language	English
Pages (from-to)	4274-4279
Number of pages	6
Journal	Organic Letters
Volume	26
Issue number	20
DOIs	https://doi.org/10.1021/acs.orglett.4c01088
State	Published - 24 May 2024

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title = "Merging of Palladium and Organocatalysis Enabled Asymmetric Decarboxylative (2+1) Cycloadditions toward Cyclopropanes",

abstract = "A cascade reaction enabling enantio- and diastereoselective construction of strained cyclopropanes is described. This asymmetric (2+1) annulation process uses vinyl methylene carbonate and 2-cyanoacrylate as reaction partners in the presence of Pd(PPh3)4 as a precatalyst and an enantioenriched phosphoramidite ligand featuring a morpholine functionality. Mechanistic investigations unveil that the PPh3 derived from the Pd(PPh3)4 and the morpholine-containing phosphoramidite work as cooperative phosphorus and Br{\o}nsted base catalysts to promote the reaction.",

author = "Biwei Yan and Pengchen Ma and Xiao Shu and Wenhao Yin and Wusheng Guo",

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year = "2024",

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doi = "10.1021/acs.orglett.4c01088",

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T1 - Merging of Palladium and Organocatalysis Enabled Asymmetric Decarboxylative (2+1) Cycloadditions toward Cyclopropanes

AU - Yan, Biwei

AU - Ma, Pengchen

AU - Shu, Xiao

AU - Yin, Wenhao

AU - Guo, Wusheng

PY - 2024/5/24

Y1 - 2024/5/24

N2 - A cascade reaction enabling enantio- and diastereoselective construction of strained cyclopropanes is described. This asymmetric (2+1) annulation process uses vinyl methylene carbonate and 2-cyanoacrylate as reaction partners in the presence of Pd(PPh3)4 as a precatalyst and an enantioenriched phosphoramidite ligand featuring a morpholine functionality. Mechanistic investigations unveil that the PPh3 derived from the Pd(PPh3)4 and the morpholine-containing phosphoramidite work as cooperative phosphorus and Brønsted base catalysts to promote the reaction.

AB - A cascade reaction enabling enantio- and diastereoselective construction of strained cyclopropanes is described. This asymmetric (2+1) annulation process uses vinyl methylene carbonate and 2-cyanoacrylate as reaction partners in the presence of Pd(PPh3)4 as a precatalyst and an enantioenriched phosphoramidite ligand featuring a morpholine functionality. Mechanistic investigations unveil that the PPh3 derived from the Pd(PPh3)4 and the morpholine-containing phosphoramidite work as cooperative phosphorus and Brønsted base catalysts to promote the reaction.

UR - https://www.scopus.com/pages/publications/85192795647

U2 - 10.1021/acs.orglett.4c01088

DO - 10.1021/acs.orglett.4c01088

M3 - 文章

C2 - 38727082

AN - SCOPUS:85192795647

SN - 1523-7060

VL - 26

SP - 4274

EP - 4279

JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

Merging of Palladium and Organocatalysis Enabled Asymmetric Decarboxylative (2+1) Cycloadditions toward Cyclopropanes

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