DMAP-Catalyzed [4 + 2] Annulation of Hex-5-en-2-ynoates with Electron-Poor Alkenes

Dongqiu Li; Jiale Wu; Lu Lu Yang; Shuangshuang Cai; Yuhai Tang; Yang Li; Silong Xu

doi:10.1021/acs.orglett.4c03842

DMAP-Catalyzed [4 + 2] Annulation of Hex-5-en-2-ynoates with Electron-Poor Alkenes

Dongqiu Li
, Jiale Wu
, Lu Lu Yang
, Shuangshuang Cai
, Yuhai Tang
, Yang Li
, Silong Xu

School of Chemistry

Xi'an Jiaotong University
Ltd.

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

4 Scopus citations

Abstract

Herein, we report a DMAP-catalyzed [4 + 2] annulation reaction of hex-5-en-2-ynoates 1 with electron-poor alkenes 2, which affords exocyclic olefinic cyclohexenes 3 in good yields and excellent regio-, diastereo-, and E/Z selectivities. Distinguished from previous allenoate- or alkynoate-based substrates, hex-5-en-2-ynoates 1 use the β- and ϵ-carbons for the bond formation, presenting new and regiodivergent C₄ synthons for Lewis base-catalyzed annulations.

Original language	English
Pages (from-to)	51-56
Number of pages	6
Journal	Organic Letters
Volume	27
Issue number	1
DOIs	https://doi.org/10.1021/acs.orglett.4c03842
State	Published - 10 Jan 2025

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title = "DMAP-Catalyzed [4 + 2] Annulation of Hex-5-en-2-ynoates with Electron-Poor Alkenes",

abstract = "Herein, we report a DMAP-catalyzed [4 + 2] annulation reaction of hex-5-en-2-ynoates 1 with electron-poor alkenes 2, which affords exocyclic olefinic cyclohexenes 3 in good yields and excellent regio-, diastereo-, and E/Z selectivities. Distinguished from previous allenoate- or alkynoate-based substrates, hex-5-en-2-ynoates 1 use the β- and ϵ-carbons for the bond formation, presenting new and regiodivergent C4 synthons for Lewis base-catalyzed annulations.",

author = "Dongqiu Li and Jiale Wu and Yang, \{Lu Lu\} and Shuangshuang Cai and Yuhai Tang and Yang Li and Silong Xu",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society.",

year = "2025",

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doi = "10.1021/acs.orglett.4c03842",

language = "英语",

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TY - JOUR

T1 - DMAP-Catalyzed [4 + 2] Annulation of Hex-5-en-2-ynoates with Electron-Poor Alkenes

AU - Li, Dongqiu

AU - Wu, Jiale

AU - Yang, Lu Lu

AU - Cai, Shuangshuang

AU - Tang, Yuhai

AU - Li, Yang

AU - Xu, Silong

PY - 2025/1/10

Y1 - 2025/1/10

N2 - Herein, we report a DMAP-catalyzed [4 + 2] annulation reaction of hex-5-en-2-ynoates 1 with electron-poor alkenes 2, which affords exocyclic olefinic cyclohexenes 3 in good yields and excellent regio-, diastereo-, and E/Z selectivities. Distinguished from previous allenoate- or alkynoate-based substrates, hex-5-en-2-ynoates 1 use the β- and ϵ-carbons for the bond formation, presenting new and regiodivergent C4 synthons for Lewis base-catalyzed annulations.

AB - Herein, we report a DMAP-catalyzed [4 + 2] annulation reaction of hex-5-en-2-ynoates 1 with electron-poor alkenes 2, which affords exocyclic olefinic cyclohexenes 3 in good yields and excellent regio-, diastereo-, and E/Z selectivities. Distinguished from previous allenoate- or alkynoate-based substrates, hex-5-en-2-ynoates 1 use the β- and ϵ-carbons for the bond formation, presenting new and regiodivergent C4 synthons for Lewis base-catalyzed annulations.

UR - https://www.scopus.com/pages/publications/85212779950

U2 - 10.1021/acs.orglett.4c03842

DO - 10.1021/acs.orglett.4c03842

M3 - 文章

C2 - 39707150

AN - SCOPUS:85212779950

SN - 1523-7060

VL - 27

SP - 51

EP - 56

JO - Organic Letters

JF - Organic Letters

IS - 1

ER -

DMAP-Catalyzed [4 + 2] Annulation of Hex-5-en-2-ynoates with Electron-Poor Alkenes

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