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An Organocatalytic Asymmetric Nazarov Cyclization

Ashok K. Basak, Naoyuki Shimada, William F. Bow, David A. Vicic and Marcus A. Tius*

*Department of Chemistry, 2545 The Mall, University of Hawaii, Honolulu, Hawaii 96822, Email: tiushawaii.edu

A. K. Basak, N. Shimada, W. F. Bow, D. A. Vicic, M. A. Tius, J. Am. Chem. Soc., 2010, 132, 8266-8267.

DOI: 10.1021/ja103028r (free Supporting Information)



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Abstract

An organocatalytic asymmetric Nazarov cyclization of diketoesters, that proceeds by means of a dual activation mechanism, gives rise to cyclic products with two adjacent quaternary asymmetric carbon atoms, one of which is an all-carbon stereocenter, with complete or nearly complete diastereoselectivity and in high enantiomeric excess.

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Cyclizations of α-Diketones to α-Hydroxycyclopentenones on Silica Gel in the Absence of Solvent

E. A. Uhrich, W. A. Batson, M. A. Tius, Synthesis, 2006, 2139-2142.


Key Words

Nazarov Cyclization, Organocatalysis


ID: J48-Y2010-1690