Catalytic Asymmetric Roskamp Reaction of Silyl Diazoalkane:
Synthesis of Enantioenriched α‑Silyl Ketone
Posted on 2017-10-20 - 15:01
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).
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Kim, Jae Yeon; Kang, Byung Chul; Ryu, Do Hyun (2017). Catalytic Asymmetric Roskamp Reaction of Silyl Diazoalkane:
Synthesis of Enantioenriched α‑Silyl Ketone. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b02928
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AUTHORS (3)
JK
Jae Yeon Kim
BK
Byung Chul Kang
DR
Do Hyun Ryu