24278-73-7Relevant academic research and scientific papers
Catalytic Enantioselective α-Ketol Rearrangement
Wu, Hua,Andres, Rémi,Wang, Qian,Zhu, Jieping
supporting information, p. 499 - 503 (2018/12/13)
A highly enantioselective α-ketol rearrangement has been developed. In the presence of a chiral Cu-bisoxazoline complex, achiral β-hydroxy-α-dicarbonyls were isomerized to chiral α-hydroxy-β-dicarbonyls and their bicyclic derivatives in excellent yields and enantioselectivities. Enantioenriched 2-acyl-2-hydroxy cyclohexan-1-ones, dihydroxyhexahydrobenzofuranones, and dihydroxyhexahydro-cycloheptafuranones, with up to three stereocenters, were readily prepared from achiral starting materials in one operation. The reaction is applicable to the desymmetrization of meso substrates and kinetic resolution of racemic alcohols.
A Nonresolutive Approach to the Preparation of Configurationally Pure Difunctional Molecules
Chillous, Sandra E.,Hart, David J.,Hutchinson, Douglas K.
, p. 5418 - 5420 (2007/10/02)
Treatment of menthone (5) with organometallic reagents affords axial tertiary alcohols of type 6 with high diastereoselectivity.Propionate 12, derived from trans-11, undergoes an enolate Claisen rearrangement with complete transfer of chirality.The use of
