Iodobenzene-Catalyzed Intramolecular Oxidative Cyclization Reactions of ß-Alkynyl β-Ketoesters

Arantxa Rodríguez; Wesley J. Moran

doi:10.1021/ol200471w

Iodobenzene-Catalyzed Intramolecular Oxidative Cyclization Reactions of ß-Alkynyl β-Ketoesters

Arantxa Rodríguez, Wesley J. Moran

School of Applied Sciences

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

56 Citations (Scopus)

Abstract

Iodobenzene is shown to catalyze the 5-exo-dig cyclization of ß-alkynyl β-ketoesters under oxidative conditions that generate hypervalent iodine species in situ. The cyclopentane products contain adjacent quaternary and tertiary stereocenters which are generated with excellent diastereoselectivity.

Original language	English
Pages (from-to)	2220-2223
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	9
Early online date	1 Apr 2011
DOIs	https://doi.org/10.1021/ol200471w
Publication status	Published - 6 May 2011

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10.1021/ol200471w

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title = "Iodobenzene-Catalyzed Intramolecular Oxidative Cyclization Reactions of {\ss}-Alkynyl β-Ketoesters",

abstract = "Iodobenzene is shown to catalyze the 5-exo-dig cyclization of {\ss}-alkynyl β-ketoesters under oxidative conditions that generate hypervalent iodine species in situ. The cyclopentane products contain adjacent quaternary and tertiary stereocenters which are generated with excellent diastereoselectivity.",

author = "Arantxa Rodr{\'i}guez and Moran, \{Wesley J.\}",

year = "2011",

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T1 - Iodobenzene-Catalyzed Intramolecular Oxidative Cyclization Reactions of ß-Alkynyl β-Ketoesters

AU - Rodríguez, Arantxa

AU - Moran, Wesley J.

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Y1 - 2011/5/6

N2 - Iodobenzene is shown to catalyze the 5-exo-dig cyclization of ß-alkynyl β-ketoesters under oxidative conditions that generate hypervalent iodine species in situ. The cyclopentane products contain adjacent quaternary and tertiary stereocenters which are generated with excellent diastereoselectivity.

AB - Iodobenzene is shown to catalyze the 5-exo-dig cyclization of ß-alkynyl β-ketoesters under oxidative conditions that generate hypervalent iodine species in situ. The cyclopentane products contain adjacent quaternary and tertiary stereocenters which are generated with excellent diastereoselectivity.

UR - https://www.scopus.com/pages/publications/79955588072

U2 - 10.1021/ol200471w

DO - 10.1021/ol200471w

M3 - Article

AN - SCOPUS:79955588072

SN - 1523-7060

VL - 13

SP - 2220

EP - 2223

JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

Iodobenzene-Catalyzed Intramolecular Oxidative Cyclization Reactions of ß-Alkynyl β-Ketoesters

Abstract

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