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Functionalization of benzothiazines via a sulfoximine stabilized vinyl carbanion

✍ Scribed by Harmata Michael

Book ID
104216789
Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
215 KB
Volume
29
Category
Article
ISSN
0040-4039

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✦ Synopsis

suuuna~: Benzothiazine Pb is readily deprotonated by n-BuLi to give the first example of a sulfoximine stabilized vinyl carbanion. The latter reacts efficiently with a variety of electrophiles.

Recently, we reported a general regioselective cyclization reaction between N-phenyl-(4-methylphenyl)sulfoximidoyl chloride 1 and alkynes which leads to benzothiazines 2 in good yield (Equation l).l The process leads to Markownikoff type addition products. While the reaction represents a powerful

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## Abstract Direct 1‐__C__‐lithiation of the readily available 2‐phenylsulfinyl‐D‐galactals 3h, 1 leads to reactive intermediates, which on reaction with glyoxal monodiethyl acetal as electrophile yield compounds 7. Subsequent __O__‐benzylation of the unprotected hydroxy group, removal of the pheny