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: tius
hawaii.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
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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.
see article for more examples
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
