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Synlett 2015; 26(01): 123-126
DOI: 10.1055/s-0034-1379489
DOI: 10.1055/s-0034-1379489
letter
Enantioselective Organocatalyzed Desymmetrization of 3-Substituted Cyclobutanones through Michael Addition to Nitroalkenes
Further Information
Publication History
Received: 11 September 2014
Accepted after revision: 13 October 2014
Publication Date:
11 November 2014 (online)


Abstract
A new procedure for the desymmetrization of prochiral 3-substituted cyclobutanones has been established through organocatalyzed Michael addition to nitroalkenes. The approach provides enantiomerically enriched 2-alkyl-3-aryl(alkyl) cyclobutanones with three contiguous stereogenic centers. The optimum conditions were determined by screening of catalyst and reaction conditions and a transition-state model is proposed to account for the observed diastereomeric and enantiomeric selectivities.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379489.
- Supporting Information