Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 354, Issue 17, Pages 3283-3290Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201200499
Keywords
asymmetric catalysis; benzoin reaction; N-heterocyclic carbene; organocatalysis; quaternary stereocenters
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Bicyclic compounds with two contiguous tetrasubstituted carbon stereocenters at bridgehead positions were synthesized by N-heterocyclic carbene (NHC)-catalyzed intramolecular crossed benzoin reactions of symmetrical compounds. This desymmetrization strategy was applied to asymmetric synthesis with chiral NHC organocatalysts. Transition-state models were proposed to explain the enantioselectivity. A tricyclic compound with three contiguous tetrasubstituted carbon stereocenters was synthesized by a stepwise strategy. The molecular structure and absolute configuration of the (+)-enantiomer of this tricyclic compound were determined by X-ray crystallographic analysis.
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