Lewis acid catalyzed cascade reaction of 3-(2-benzenesulfonamide)propargylic alcohols to spiro[indene-benzosultam]s

Lang Sun; Yuanxun Zhu; Jing Wang; Ping Lu; Yanguang Wang

doi:10.1021/ol503316e

Lewis acid catalyzed cascade reaction of 3-(2-benzenesulfonamide)propargylic alcohols to spiro[indene-benzosultam]s

Lang Sun
, Yuanxun Zhu
, Jing Wang
, Ping Lu^*
, Yanguang Wang

^*Corresponding author for this work

Zhejiang University

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

32 Citations (Scopus)

Abstract

A highly efficient and convenient construction of the spiro[indene-benzosultam] skeleton from propargylic alcohols has been developed. The reaction proceeded in a Lewis acid catalyzed cascade process, including the trapping of allene carbocation with sulfonamide, electrophilic cyclization, and intramolecular Friedel-Crafts alkylation. In the presence of NIS or NBS, iodo/bromo-substituted spiro[indene-benzosultam]s could be prepared in excellent yields.

Original language	English
Pages (from-to)	242-245
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	2
DOIs	https://doi.org/10.1021/ol503316e
Publication status	Published - 16 Jan 2015
Externally published	Yes

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10.1021/ol503316e

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title = "Lewis acid catalyzed cascade reaction of 3-(2-benzenesulfonamide)propargylic alcohols to spiro[indene-benzosultam]s",

abstract = "A highly efficient and convenient construction of the spiro[indene-benzosultam] skeleton from propargylic alcohols has been developed. The reaction proceeded in a Lewis acid catalyzed cascade process, including the trapping of allene carbocation with sulfonamide, electrophilic cyclization, and intramolecular Friedel-Crafts alkylation. In the presence of NIS or NBS, iodo/bromo-substituted spiro[indene-benzosultam]s could be prepared in excellent yields.",

author = "Lang Sun and Yuanxun Zhu and Jing Wang and Ping Lu and Yanguang Wang",

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year = "2015",

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T1 - Lewis acid catalyzed cascade reaction of 3-(2-benzenesulfonamide)propargylic alcohols to spiro[indene-benzosultam]s

AU - Sun, Lang

AU - Zhu, Yuanxun

AU - Wang, Jing

AU - Lu, Ping

AU - Wang, Yanguang

PY - 2015/1/16

Y1 - 2015/1/16

N2 - A highly efficient and convenient construction of the spiro[indene-benzosultam] skeleton from propargylic alcohols has been developed. The reaction proceeded in a Lewis acid catalyzed cascade process, including the trapping of allene carbocation with sulfonamide, electrophilic cyclization, and intramolecular Friedel-Crafts alkylation. In the presence of NIS or NBS, iodo/bromo-substituted spiro[indene-benzosultam]s could be prepared in excellent yields.

AB - A highly efficient and convenient construction of the spiro[indene-benzosultam] skeleton from propargylic alcohols has been developed. The reaction proceeded in a Lewis acid catalyzed cascade process, including the trapping of allene carbocation with sulfonamide, electrophilic cyclization, and intramolecular Friedel-Crafts alkylation. In the presence of NIS or NBS, iodo/bromo-substituted spiro[indene-benzosultam]s could be prepared in excellent yields.

UR - https://www.scopus.com/pages/publications/84921274003

U2 - 10.1021/ol503316e

DO - 10.1021/ol503316e

M3 - Article

C2 - 25541815

AN - SCOPUS:84921274003

SN - 1523-7060

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JO - Organic Letters

JF - Organic Letters

IS - 2

ER -

Lewis acid catalyzed cascade reaction of 3-(2-benzenesulfonamide)propargylic alcohols to spiro[indene-benzosultam]s

Abstract

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