Enamine-Iminium Ion Nazarov Cyclization of alpha-Ketolenones

The mono-triflate salts of some chiral nonracemic 1,2-diamines react with alpha-ketoenones in a stoichiometric reaction to form products of the Nazarov cyclization in high enantiomeric ratios. The mechanism appears to involve rearrangement of an enamine-iminium ion.

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 12; no. 3; pp. 440 - 443
Main Authors Bow, William F., Basak, Ashok K., Jolit, Anais, Vicic, David A., Tius, Marcus A.
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 05.02.2010
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ELECTROCYCLIZATION
ACIDS
DIENONES
Online AccessGet full text

Cover

More Information
Summary:The mono-triflate salts of some chiral nonracemic 1,2-diamines react with alpha-ketoenones in a stoichiometric reaction to form products of the Nazarov cyclization in high enantiomeric ratios. The mechanism appears to involve rearrangement of an enamine-iminium ion.
Bibliography:NIH RePORTER
ISSN:1523-7060
1523-7052
DOI:10.1021/ol9025765