Issue 23, 1990

A new approach to (Z)-vinyloxyboranes via 1,4 hydroboration of (E)-α,β-unsaturated ketones. Synthesis of syn aldols

Abstract

(Z)-Vinyloxy boranes are obtained via 1,4-hydroboration of acyclic disubstituted (E)-α,β-unsaturated ketones with dicyclohexylborane or diisopinocampheylborane in tetrahydrofuran, CH2Cl2 or CHCl3 at 20 °C; treatment of the hydroboration mixture with an aldehyde allows pure syn aldols to be synthesized in good yields, and in excellent enantiomeric excesses, using the latter borane.

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1990, 1680-1681

A new approach to (Z)-vinyloxyboranes via 1,4 hydroboration of (E)-α,β-unsaturated ketones. Synthesis of syn aldols

G. P. Boldrini, F. Mancini, E. Tagliavini, C. Trombini and A. Umani-Ronchi, J. Chem. Soc., Chem. Commun., 1990, 1680 DOI: 10.1039/C39900001680

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