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2004
Alcohols
Q 0230
49- 076
Highly Selective Reduction of Acyclic β-Alkoxy Ketones to Protected syn-1,3-Diols. — A direct and highly selective synthesis of protected syn-1,3-diols from the corresponding protected β-hydroxy ketones by way of a cyclic oxocarbenium ion is demonstrated. The reaction affords the products in yields from 69 to 94% and with diastereoselectivities >200:1. The attempted reduction of α,β-unsaturated ketone (VI) provides a complex mixture of products under all conditions examined. — (CULLEN, A.
J.; SAMMAKIA*, T.; Org. Lett. 6 (2004) 18, 3143-3145; Dep. Chem. Biochem.,
Univ. Colo., Boulder, CO 80309, USA; Eng.) — Steudel
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