Catalyst-Controlled Chemoselective All-Alkene [2 + 2 + 2] and [2 + 2] Cyclizations of Enamides with Electron-Deficient Alkenes

Song Wei; Lei Yin; Sunewang R. Wang; Yong Tang

doi:10.1021/acs.orglett.9b00209

Catalyst-Controlled Chemoselective All-Alkene [2 + 2 + 2] and [2 + 2] Cyclizations of Enamides with Electron-Deficient Alkenes

Song Wei
, Lei Yin
, Sunewang R. Wang^*
, Yong Tang

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

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

33 Scopus citations

Abstract

In the presence of 4 Å MS, both all-alkene [2 + 2 + 2] and [2 + 2] cyclizations of dimethyl methylenemalonate (DMM) with N-sulfonyl enamides were selectively achieved under In(OTf) ₃ and Cu(OTf) ₂ catalysis, respectively. In(OTf) ₃ -catalyzed [4 + 2] cyclization of the sulfonylamidocyclobutanes with another molecule of DMM or other electron-deficient alkenes was also reported.

Original language	English
Pages (from-to)	1458-1462
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.9b00209
State	Published - 1 Mar 2019

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title = "Catalyst-Controlled Chemoselective All-Alkene [2 + 2 + 2] and [2 + 2] Cyclizations of Enamides with Electron-Deficient Alkenes",

abstract = " In the presence of 4 {\AA} MS, both all-alkene [2 + 2 + 2] and [2 + 2] cyclizations of dimethyl methylenemalonate (DMM) with N-sulfonyl enamides were selectively achieved under In(OTf) 3 and Cu(OTf) 2 catalysis, respectively. In(OTf) 3 -catalyzed [4 + 2] cyclization of the sulfonylamidocyclobutanes with another molecule of DMM or other electron-deficient alkenes was also reported.",

author = "Song Wei and Lei Yin and Wang, \{Sunewang R.\} and Yong Tang",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = mar,

day = "1",

doi = "10.1021/acs.orglett.9b00209",

language = "英语",

volume = "21",

pages = "1458--1462",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "5",

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TY - JOUR

T1 - Catalyst-Controlled Chemoselective All-Alkene [2 + 2 + 2] and [2 + 2] Cyclizations of Enamides with Electron-Deficient Alkenes

AU - Wei, Song

AU - Yin, Lei

AU - Wang, Sunewang R.

AU - Tang, Yong

PY - 2019/3/1

Y1 - 2019/3/1

N2 - In the presence of 4 Å MS, both all-alkene [2 + 2 + 2] and [2 + 2] cyclizations of dimethyl methylenemalonate (DMM) with N-sulfonyl enamides were selectively achieved under In(OTf) 3 and Cu(OTf) 2 catalysis, respectively. In(OTf) 3 -catalyzed [4 + 2] cyclization of the sulfonylamidocyclobutanes with another molecule of DMM or other electron-deficient alkenes was also reported.

AB - In the presence of 4 Å MS, both all-alkene [2 + 2 + 2] and [2 + 2] cyclizations of dimethyl methylenemalonate (DMM) with N-sulfonyl enamides were selectively achieved under In(OTf) 3 and Cu(OTf) 2 catalysis, respectively. In(OTf) 3 -catalyzed [4 + 2] cyclization of the sulfonylamidocyclobutanes with another molecule of DMM or other electron-deficient alkenes was also reported.

UR - https://www.scopus.com/pages/publications/85062353099

U2 - 10.1021/acs.orglett.9b00209

DO - 10.1021/acs.orglett.9b00209

M3 - 文章

C2 - 30789744

AN - SCOPUS:85062353099

SN - 1523-7060

VL - 21

SP - 1458

EP - 1462

JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

Catalyst-Controlled Chemoselective All-Alkene [2 + 2 + 2] and [2 + 2] Cyclizations of Enamides with Electron-Deficient Alkenes

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