Nucleophilic Migratory Cyclopropenation of Activated Alkynes: A Nonmetal Approach to Unbiased Cyclopropenes

Pengwei Tan; Haoran Wang; Sunewang R. Wang

doi:10.1021/acs.orglett.1c00498

Nucleophilic Migratory Cyclopropenation of Activated Alkynes: A Nonmetal Approach to Unbiased Cyclopropenes

Pengwei Tan, Haoran Wang, Sunewang R. Wang^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

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

21 Scopus citations

Abstract

An unprecedented reductive [2 + 1] annulation of α-keto esters with alkynones mediated by P(NMe2)3 is described. Although this nonmetal cyclopropenation is a nucleophilic process, attributed to the ester migration via a formal [2 + 2] cycloaddition reaction of Kukhtin-Ramirez adducts and alkynones followed by a fragmentation, cyclopropenes with an unbiased alkene scaffold are formed in good to excellent yields, thus providing a promising complementarity to electrophilic metal-catalyzed cyclopropenation.

Original language	English
Pages (from-to)	2590-2594
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	7
DOIs	https://doi.org/10.1021/acs.orglett.1c00498
State	Published - 2 Apr 2021

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title = "Nucleophilic Migratory Cyclopropenation of Activated Alkynes: A Nonmetal Approach to Unbiased Cyclopropenes",

abstract = "An unprecedented reductive [2 + 1] annulation of α-keto esters with alkynones mediated by P(NMe2)3 is described. Although this nonmetal cyclopropenation is a nucleophilic process, attributed to the ester migration via a formal [2 + 2] cycloaddition reaction of Kukhtin-Ramirez adducts and alkynones followed by a fragmentation, cyclopropenes with an unbiased alkene scaffold are formed in good to excellent yields, thus providing a promising complementarity to electrophilic metal-catalyzed cyclopropenation.",

author = "Pengwei Tan and Haoran Wang and Wang, \{Sunewang R.\}",

note = "Publisher Copyright: {\textcopyright} ",

year = "2021",

month = apr,

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doi = "10.1021/acs.orglett.1c00498",

language = "英语",

volume = "23",

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journal = "Organic Letters",

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T1 - Nucleophilic Migratory Cyclopropenation of Activated Alkynes

T2 - A Nonmetal Approach to Unbiased Cyclopropenes

AU - Tan, Pengwei

AU - Wang, Haoran

AU - Wang, Sunewang R.

N1 - Publisher Copyright: ©

PY - 2021/4/2

Y1 - 2021/4/2

N2 - An unprecedented reductive [2 + 1] annulation of α-keto esters with alkynones mediated by P(NMe2)3 is described. Although this nonmetal cyclopropenation is a nucleophilic process, attributed to the ester migration via a formal [2 + 2] cycloaddition reaction of Kukhtin-Ramirez adducts and alkynones followed by a fragmentation, cyclopropenes with an unbiased alkene scaffold are formed in good to excellent yields, thus providing a promising complementarity to electrophilic metal-catalyzed cyclopropenation.

AB - An unprecedented reductive [2 + 1] annulation of α-keto esters with alkynones mediated by P(NMe2)3 is described. Although this nonmetal cyclopropenation is a nucleophilic process, attributed to the ester migration via a formal [2 + 2] cycloaddition reaction of Kukhtin-Ramirez adducts and alkynones followed by a fragmentation, cyclopropenes with an unbiased alkene scaffold are formed in good to excellent yields, thus providing a promising complementarity to electrophilic metal-catalyzed cyclopropenation.

UR - https://www.scopus.com/pages/publications/85103800295

U2 - 10.1021/acs.orglett.1c00498

DO - 10.1021/acs.orglett.1c00498

M3 - 文章

C2 - 33754741

AN - SCOPUS:85103800295

SN - 1523-7060

VL - 23

SP - 2590

EP - 2594

JO - Organic Letters

JF - Organic Letters

IS - 7

ER -

Nucleophilic Migratory Cyclopropenation of Activated Alkynes: A Nonmetal Approach to Unbiased Cyclopropenes

Abstract

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