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Enantioselective organocatalytic Michael-Wittig-Michael-Michael reaction: dichotomous construction of pentasubstituted cyclopentanecarbaldehydes and pentasubstituted cyclohexanecarbaldehydes

Hong, B.-C.; Nimje, R.Y.; Lin, C.-W.; Liao, J.-H.

Organic Letters 13(6): 1278-1281

2011


ISSN/ISBN: 1523-7052
PMID: 21348453
DOI: 10.1021/ol1030487
Accession: 052954515

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Michael addition of carbethoxymethylenetriphenylphosphorane (a Wittig reagent) to nitroalkenes, followed by a reaction with ethyl formylformate and cinnamaldehydes, or formaldehyde and cinnamaldehydes, provided the respective pentasubstituted cyclopentanecarbaldehydes bearing a quaternary carbon center and pentasubstituted cyclohexanecarbaldehydes having five contiguous stereocenters with excellent enantioselectivities (up to >99% ee).

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