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Enantioselective Synthesis of 1,5-anti- and 1,5-syn-Diols Using a Highly Diastereoselective One-Pot Double Allylboration Reaction Sequence

Eric M. Flamme and William R. Roush*

*Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055, Email:

E. M. Flamme, W. R. Roush, J. Am. Chem. Soc., 2002, 124, 13644-13645.

DOI: 10.1021/ja028055j

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Highly diastereo- and enantioselective syntheses of 1,5-disubstituted (E)-1,5-anti-pent-2-endiols and (Z)-1,5-syn-pent-2-endiols have been achieved via the one-pot coupling of two different aldehydes with bifunctional γ-boryl-substituted allylborane reagents, which were generated in situ by the hydroboration of allenes with diisopinocampheylborane. The stereospecificity is discussed.

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Key Words

Hydroboration, Allylic Alcohols, Homoallylic Alcohols

ID: J48-Y2002-1340