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Synfacts 2005(3): 0349-0349  
DOI: 10.1055/s-2005-921649
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Organo-Cascade Catalysis of α,β-Unsaturated Aldehydes

Contributor(s): Benjamin List, Nolwenn J. A. Martin
Y. Huang, A. M. Walji, C. H. Larsen, D. W. C. MacMillan*
California Institute of Technology, Pasadena, USA
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Publikationsverlauf

Publikationsdatum:
22. November 2005 (online)

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Significance

The authors developed a new approach to cascade catalysis. Using a single imidazolidinone catalyst, involving iminium (LUMO-lowering) and enamine (HOMO-raising) catalysis, a large diversity of nucleophiles (furans, thiophenes, indoles, butenolides, hydride sources, tertiary amino lactone equivalents) and electrophiles (fluo­rinating and chlorinating reagents) undergo highly enantioselective sequential addition with α,β-unsaturated aldehydes (÷99% ee in all cases).