BCl3- and TiCl4-Mediated Reductions of β-Hydroxy Ketones
The Journal of Organic Chemistry1996Vol. 61(3), pp. 868–873
Citations Over TimeTop 10% of 1996 papers
Abstract
Syn-selective reduction protocols for β-hydroxy ketones are described exploiting the intermediacy of titanium and boron chelates derived from TiCl4 and BCl3, respectively. Reductions are conducted at −78 °C in CH2Cl2 using a wide range of CH2Cl2-soluble reducing agents. Added acid-scavenging agents are detrimental to reaction selectivity. An A(1,3)-like interaction involving the stereocenter responsible for asymmetric induction provides conformational biasing of the intermediate chelates necessary for high diastereoselectivity.
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