An Organocatalyzed Michael Addition-Cyclization
Sequence to Spirolactones

S. Sternativo; A. Calandriello; F. Constantino; L. Testaferri; M. Tiecco; F. Marini

doi:10.1055/s-0031-1289350

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Synfacts 2011(12): 1349-1349
DOI: 10.1055/s-0031-1289350

Metal-Mediated Synthesis

An Organocatalyzed Michael Addition-Cyclization Sequence to Spirolactones

Contributor(s): Paul Knochel, Thomas Kunz
S. Sternativo, A. Calandriello, F. Constantino, L. Testaferri, M. Tiecco, F. Marini*
Università di Perugia, Italy

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Publication History

Publication Date:
18 November 2011 (online)

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Significance

The authors describe the first highly enantioselective preparation of spirolactones using racemic cyclic β-keto esters and vinyl selenone. This organocatalyzed one-pot Michael addition-cyclization sequence affords various spirolactones in high yields with excellent enantioselectivity.