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Synfacts 2006(10): 1022-1022  
DOI: 10.1055/s-2006-949287
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Synthesis of syn-anti Stereotriad Building Blocks

Contributor(s): Mark Lautens, Frédéric Ménard
K. A. Parker*, H. Cao
State University of New York at Stony Brook, USA
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Publication History

Publication Date:
21 September 2006 (online)

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Significance

Recent methodologies that give access to chiral (Z)-allylic alcohols make the ‘Midland sequence’ (1 ♢ 4) synthetically more useful (D. J. S. Tsai, M. M. Midland J. Am. Chem. Soc. 1985, 107, 3915-3918). The key intermediate 2 was prepared by Oppolzer’s asymmetric addition of an alkenylzinc reagent to aldehydes (W. Oppolzer, R. N. Radinov Tetrahedron Lett. 1991, 32, 5777-5780). The 2,3-Wittig rearrangement proceeds with excellent stereoselectivity to set two stereocenters while the third one is controlled by a diastereo­selective hydroboration.