Syn-selective reduction protocols for β-hydroxy ketones are described exploiting the intermediacy of titanium and boron chelates derived from TiCl 4 and BCl 3, respectively. Reductions are conducted at −78 °C in CH 2 Cl 2 using a wide range of CH 2 Cl 2 -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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Sarko et al. (1996) studied this question.
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