Synfacts 2006(6): 0579-0579  
DOI: 10.1055/s-2006-934478
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Allylation of Aldehydes Using a Chiral Cr(III) Complex

Contributor(s): Mark Lautens, Andrew Martins
G. Xia, H. Yamamoto*
The University of Chicago, USA
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Publikationsverlauf

Publikationsdatum:
19. Mai 2006 (online)

Significance

Under mild Lewis acidic conditions, a wide variety of aldehydes were converted into the corresponding enantioenriched homoallylic alcohols using simple alkyl halides and a chromium complex. Yields and enantioselectivities are generally high for allylation, with good anti:syn ratios for crotylation in addition to high enantioselectivities for each diastereomer. The reaction tolerates a range of aromatic substitutents, although neither substrates with strongly electron-withdrawing nor Lewis basic substitutents were reported.