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Synfacts 2011(2): 0164-0164  
DOI: 10.1055/s-0030-1259339
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Intermolecular Hydroacylation of Homoallylic Sulfides

Contributor(s): Mark Lautens, Norman Nicolaus
M. M. Coulter, K. G. M. Kou, B. Galligan, V. M. Dong*
University of Toronto, Canada
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Publikationsdatum:
19. Januar 2011 (online)

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Significance

Asymmetric hydroacylations are extremely atom-economic reactions for the preparation of chiral ketones starting from alkenes and aldehydes. The intermolecular hydroacylation of terminal olefins usually gives the linear (achiral) products or mixtures of regioisomers. Herein, an intermolecular asymmetric and heteroatom-­directed rhodium-catalyzed hydroacylation between salicylaldehydes 1 and homoallylic sulfides 2 has been developed. The methodology allows the formation of α-branched isomers 3 in excellent regio- and enantioselectivities.