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Synfacts 2013; 9(7): 0737
DOI: 10.1055/s-0033-1339171
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Cr/Salen-Catalyzed Nazarov Cyclization of Dienones

Contributor(s):
Hisashi Yamamoto
,
Jiajing Tan
Hutson GE, Türkmen YE, Rawal VH * The University of Chicago, USA
Salen Promoted Enantioselective Nazarov Cyclizations of Activated and Unactivated Dienones.

J. Am. Chem. Soc. 2013;
135: 4988-4991
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Further Information

Publication History

Publication Date:
17 June 2013 (online)

 
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Key words

chromium - salen - Nazarov cyclization - dienones

Significance

Rawal and co-workers describe the highly enantioselective Cr/salen-catalyzed ­Nazarov cyclization of both activated and unactivated dienones, giving the desired hydrindenone products with three contiguous chiral centers in moderate to good yields and stereoselectivities.


 

Comment

This paper represents the first example of highly enantioselective Nazarov reactions of unactivated dienones. A one-point activation mode was proposed and a counter-clockwise conrotatory cyclization would release the R group into a less sterically congested environment.


 

 


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