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
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