3 years ago

Catalytic Asymmetric Roskamp Reaction of Silyl Diazoalkane: Synthesis of Enantioenriched α-Silyl Ketone

Catalytic Asymmetric Roskamp Reaction of Silyl Diazoalkane: Synthesis of Enantioenriched α-Silyl Ketone
Jae Yeon Kim, Do Hyun Ryu, Byung Chul Kang
A catalytic enantioselective Roskamp reaction of silyl diazoalkane to synthesize a highly optically active α-silyl ketone from aldehydes is described. In the presence of a chiral oxazaborolidinium ion catalyst, the reaction provides α-chiral silyl ketones with good yields (up to 97%) and high enantioselectivities (up to >99% ee). In addition, a one-pot procedure using an asymmetric Roskamp/reduction strategy gives highly optically active syn-β-hydroxysilane in good yields (up to 94%) with high enantioselectivities (up to 99% ee) and syn stereoselectivities (>20:1).

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02928

DOI: 10.1021/acs.orglett.7b02928

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