A new approach to (Z)-vinyloxyboranes via 1,4 hydroboration of (E)-α,β-unsaturated ketones. Synthesis of syn aldols
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 23,p. 1680-1681
- https://doi.org/10.1039/c39900001680
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.Keywords
This publication has 15 references indexed in Scilit:
- The Michael-type Reaction of B-Iodo-9-BBN/Ethoxyethyne Adduct to α,β-Unsaturated Ketones. A Selective Synthesis of δ-Keto EstersChemistry Letters, 1989
- Organoboron compounds in organic synthesis. 4. Asymmetric aldol reactionsJournal of the American Chemical Society, 1986
- Improved procedures for the synthesis of diisopinocampheylborane of high optical purityThe Journal of Organic Chemistry, 1984
- Enantioselective aldol reactions with high threo or erythro selectivity using boron azaenolatesJournal of the American Chemical Society, 1981
- Enantioselective aldol condensations. 2. Erythro-selective chiral aldol condensations via boron enolatesJournal of the American Chemical Society, 1981
- Selective reductions. 22. Facile reduction of .alpha.,.beta.-unsaturated aldehydes and ketones with 9-borabicyclo[3.3.1]nonane. A remarkably convenient procedure for the selective conversion of conjugated aldehydes and ketones to the corresponding allylic alcohols in the presence of other functional groupsThe Journal of Organic Chemistry, 1977
- Conjugate addition of B-1-alkynyl-9-borabicyclo[3.3.1]-nonanes to .alpha.,.beta.-unsaturated ketones. A convenient synthesis of .gamma.,.delta.-acetylenic ketonesJournal of the American Chemical Society, 1977
- Conjugate addition of B-alkenyl-9-borabicyclo[3.3.1]nonanes to methyl vinyl ketone. A convenient synthesis of .gamma.,.delta.-unsaturated ketonesJournal of the American Chemical Society, 1976
- Borverbindungen, XXXII1) An der Vinylgruppe substituierte Diäthyl(vinyloxy)borane aus Ketonen und Triäthylboran durch katalysierte EnolyseEuropean Journal of Organic Chemistry, 1975
- Acyl peroxide and photochemical induced reactions of organoboranes with the inert .alpha.,.beta.-unsaturated carbonyl derivativesJournal of the American Chemical Society, 1970