One‐Pot Enol Silane Formation/Mukaiyama–Mannich Addition of Ketones, Amides, and Thioesters to Nitrones in the Presence of Trialkylsilyl Trifluoromethanesulfonates | Zendy

Downey C. Wade | Zendy; Dombrowski Carolyn M. | Zendy; Maxwell Erin N. | Zendy; Safran Chelsea L. | Zendy; Akomah Odamea A. | Zendy

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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.

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