ol7b02928_si_001.pdf (5.01 MB)
Catalytic Asymmetric Roskamp Reaction of Silyl Diazoalkane: Synthesis of Enantioenriched α‑Silyl Ketone
journal contribution
posted on 2017-10-20, 15:01 authored by Jae Yeon Kim, Byung Chul Kang, Do Hyun RyuA 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).