Stereoseletive Reduction of β-Hydroxy Ketones to 1,3-Diols with the Aid of a Terphenylboronic Acid
- 1 July 1996
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 25 (7) , 539-540
- https://doi.org/10.1246/cl.1996.539
Abstract
1-Hydroxy-6,8-diphenyl-1,2,3,4-tetrahydro-2-oxa-1-boranaphthalene (terphenylboronic acid 1), is employed for stereoselective reduction of acyclic and cyclic β-hydroxy ketones. The terphenylboronic acid 1 and acyclic β-hydroxy ketones 2 are converted to the corresponding boronates by azeotropic removal of water. The resulting boronates are treated in situ with reducing reagents to give syn 1,3-diols 3 almost exclusively. Anti α-substituted β-hydroxy ketones 8 are also reduced to give anti, anti 1,3-diol 9 stereoselectively. Furthermore, the reduction of 3-hydroxy-1-cyclopentanone gives a cis diol 11 in high selectivity.Keywords
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