Catalytic Diastereoselective [5 + 2] Annulation of N-Acryloyl Indoles with Cyclic Sulfonyl Enamides: Facile Access to Isoeburnamonine

Song Wei; Long Zheng; Sunewang R. Wang; Yong Tang

doi:10.1021/acs.orglett.9b04556

Catalytic Diastereoselective [5 + 2] Annulation of N-Acryloyl Indoles with Cyclic Sulfonyl Enamides: Facile Access to Isoeburnamonine

Song Wei, Long Zheng, Sunewang R. Wang^*, Yong Tang

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

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

13 Scopus citations

Abstract

ZnBr₂-catalyzed stereoselective [5 + 2] annulation of N-acryloyl indoles with cyclic sulfonyl enamides is reported, providing a concise and efficient synthesis of isoeburnamonine, which is the key intermediate for norvincamine. Both [2 + 2] and [4 + 2] cycloadducts, depending on the ring size of the enamides, have been shown to be the important intermediates for this [5 + 2] annulation.

Original language	English
Pages (from-to)	1013-1017
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	3
DOIs	https://doi.org/10.1021/acs.orglett.9b04556
State	Published - 7 Feb 2020

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title = "Catalytic Diastereoselective [5 + 2] Annulation of N-Acryloyl Indoles with Cyclic Sulfonyl Enamides: Facile Access to Isoeburnamonine",

abstract = "ZnBr2-catalyzed stereoselective [5 + 2] annulation of N-acryloyl indoles with cyclic sulfonyl enamides is reported, providing a concise and efficient synthesis of isoeburnamonine, which is the key intermediate for norvincamine. Both [2 + 2] and [4 + 2] cycloadducts, depending on the ring size of the enamides, have been shown to be the important intermediates for this [5 + 2] annulation.",

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

note = "Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

year = "2020",

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doi = "10.1021/acs.orglett.9b04556",

language = "英语",

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T1 - Catalytic Diastereoselective [5 + 2] Annulation of N-Acryloyl Indoles with Cyclic Sulfonyl Enamides

T2 - Facile Access to Isoeburnamonine

AU - Wei, Song

AU - Zheng, Long

AU - Wang, Sunewang R.

AU - Tang, Yong

PY - 2020/2/7

Y1 - 2020/2/7

N2 - ZnBr2-catalyzed stereoselective [5 + 2] annulation of N-acryloyl indoles with cyclic sulfonyl enamides is reported, providing a concise and efficient synthesis of isoeburnamonine, which is the key intermediate for norvincamine. Both [2 + 2] and [4 + 2] cycloadducts, depending on the ring size of the enamides, have been shown to be the important intermediates for this [5 + 2] annulation.

AB - ZnBr2-catalyzed stereoselective [5 + 2] annulation of N-acryloyl indoles with cyclic sulfonyl enamides is reported, providing a concise and efficient synthesis of isoeburnamonine, which is the key intermediate for norvincamine. Both [2 + 2] and [4 + 2] cycloadducts, depending on the ring size of the enamides, have been shown to be the important intermediates for this [5 + 2] annulation.

UR - https://www.scopus.com/pages/publications/85079089008

U2 - 10.1021/acs.orglett.9b04556

DO - 10.1021/acs.orglett.9b04556

M3 - 文章

C2 - 31971396

AN - SCOPUS:85079089008

SN - 1523-7060

VL - 22

SP - 1013

EP - 1017

JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

Catalytic Diastereoselective [5 + 2] Annulation of N-Acryloyl Indoles with Cyclic Sulfonyl Enamides: Facile Access to Isoeburnamonine

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