alfa-Ketosulphides of benzothiazole 1 react with allylic carbonates in the presence of palladium acetate in dichloromethane under mild conditions affording alfa- and alfa,alfa-diallylated ketosulphides 2 in high yields. Reductive desulphurization of 2a-d with tributyltin hydride gives diallylated ketones 3s-d, whereas reduction of mono-allylated Ze-k with sodium borohydride in isopropanol affords ally1 episulphides 4e-k prevalently as (Z)-isomers which can be transformed stcteoselectively into dienes.
Allylated Ketosulphides of Benzothiazole as Intermediates for Stereoselective Synthesis of Allyl Ketones, Allyl Thiiranes and Dienes
NACCI, Angelo;
1996-01-01
Abstract
alfa-Ketosulphides of benzothiazole 1 react with allylic carbonates in the presence of palladium acetate in dichloromethane under mild conditions affording alfa- and alfa,alfa-diallylated ketosulphides 2 in high yields. Reductive desulphurization of 2a-d with tributyltin hydride gives diallylated ketones 3s-d, whereas reduction of mono-allylated Ze-k with sodium borohydride in isopropanol affords ally1 episulphides 4e-k prevalently as (Z)-isomers which can be transformed stcteoselectively into dienes.File in questo prodotto:
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