Organic Chemistry Portal

Abstracts

Search:

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: roushumich.edu

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

DOI: 10.1021/ja028055j (free Supporting Information)


see article for more examples

Abstract

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.

see article for more reactions and examples



Key Words

Hydroboration, Allylic Alcohols, Homoallylic Alcohols


ID: J48-Y2002-1340