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AldehydesQ 0320 DOI: 10.1002/chin.201001081

Asymmetric Organocatalytic Formal Alkynylation and Alkenylation of α,β-Un-saturated Aldehydes. — A new type of nucleophiles, i.e. β-keto heterocyclic sulfones reacts under mild organocatalytic conditions with α ,β-unsaturated aldehydes to the cor-responding Michael intermediates with high stereoselectivity. The latter can be con-verted into alkynes or alkenes based on new developments of the Smiles rearrangement through a process parallel to the Julia—Kocienski reaction. — (NIELSEN, M.; JACOBSEN, C. B.; PAIXIAO, M. W.; HOLUB, N.; JOERGENSEN*, K. A.; J. Am. Chem. Soc. 131 (2009) 30, 10581-10586; Dep. Chem., Univ. Aarhus, DK-8000 Aarhus, Den.; Eng.) — Bartels

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ChemInform 2010, 41, issue 01 © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim