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Trimethylsilyloxide‐Catalysed Peterson Olefinations with 2,2‐Bis(trimethylsilyl)‐1,3‐dithiane
Author(s) -
Manvar Atul,
O'Shea Donal F.
Publication year - 2015
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.201501185
Subject(s) - dithiane , chemistry , carbanion , trimethylsilyl , ketene , reagent , yield (engineering) , silylation , organic synthesis , organic chemistry , medicinal chemistry , catalysis , materials science , metallurgy
The synthesis of the reagent 2,2‐bis(trimethylsilyl)‐1,3‐dithiane was directly achieved in an excellent yield from 1,3‐dithiane in one step. The bench‐stable reagent can be utilized for Peterson olefinations using either TMSOK/Bu 4 NCl or fluoride ion as promoter of α‐silyl carbanion formation, thereby generating ketene dithioacetals, which are versatile intermediates in organic synthesis. Olefination reactions were successfully achieved with aromatic, heteroaromatic, aliphatic aldehydes and ketones.