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One‐Pot Enol Silane Formation/Mukaiyama–Mannich Addition of Ketones, Amides, and Thioesters to Nitrones in the Presence of Trialkylsilyl Trifluoromethanesulfonates
Author(s) -
Downey C. Wade,
Dombrowski Carolyn M.,
Maxwell Erin N.,
Safran Chelsea L.,
Akomah Odamea A.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300691
Subject(s) - chemistry , enol , silylation , silanes , silane , trimethylsilyl , trimethylsilyl trifluoromethanesulfonate , organic chemistry , trifluoromethanesulfonate , yield (engineering) , medicinal chemistry , catalysis , materials science , metallurgy
Ketones, amides, and thioesters form enol silanes and add to N ‐phenylnitrones in one pot in the presence of trimethylsilyl trifluoromethanesulfonate and trialkylamine. The reaction is general to a range of silyl trifluoromethanesulfonates and N ‐phenylnitrones. The β‐(silyloxy)amino carbonyl products are stable to chromatography and can be isolated in 63–99 % yield.