Asymmetric reduction of carbonyl with CBS reagent

Asymmetric reduction of carbonyl with CBS reagent

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This reduction works best when the two carbonyl substituents are well-differentiated sterically – ie Ph and Me. When the carbonyl oxygen is complexed to the boron it becomes electrophilic enough to be reduced by the weak hydride source. The hydride itself is delivered via a six-membered cyclic transition state. The enantioselectivity arises from the preference of the larger carbonyl substitutent for the pseudoequatorial position of the ring.

J. Vargas-Caporali and E. Juaristi, Synthesis (Stuttg)., 2016, 48, 3890–3906.

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