Vincent Reboul

Synthesis of 1,3-thiazines by a three-component reaction and their transformations into β-lactam-condensed 1,3-thiazine and 1,4-thiazepine derivatives

GRAPHICAL ABSTRACT ABSTRACT Variously substituted 1,3-thiazines have been prepared by a three-component reaction involving a thioamide, an aldehyde, and an alkene. Two diastereomeric thiazines were transformed by stereoselective Staudinger reaction into the corresponding chloro-β-lactam-condensed-1,3-thiazines, and one of them was rearranged in basic media to afford a highly substituted 1,4-thiazepine. Several of the obtained compounds (six 1,3-thiazines and one β-lactam-condensed-1,3-thiazine) were analyzed by X-ray crystallography, which enabled to assign their spatial arrangement and stereochemistry.

One-Pot Synthesis of Aryl- and Alkyl S-Perfluoroalkylated NH-Sulfoximines from Sulfides

A general efficient one-pot synthesis of S-perfluoroalkylated NH-sulfoximines from sulfides has been developed using phenyliodine diacetate (PIDA) and ammonium carbamate. Remarkable rate enhancement with trifluoroethanol was observed, presumably due to H-bonding effects. These mild and metal-free conditions are compatible with -CH2 F, -CFCl2 , -CF2 H, -CF2 Br, -C4 F9 , and -CF3 groups, in both the alkyl- and aryl series. Based on a 19 F NMR analysis, a λ6 -acetoxysulfanenitrile intermediate was proposed.

8.15 Reduction of S O and SO 2 to S, S–X to S–H, and P O to P

This chapter describes procedures for the reduction of sulfur- and phosphorus-centered functional groups. It covers the most relevant advances in the field after the first edition of COS in 1991. The material has been organized on the basis of the nature of the substrate and the type of reducing agent, rather than on the mechanism of the process.

A straightforward asymmetric synthesis of 1,2-disubstituted ferrocenylalkyl amines with the unusual (SFc,S) configuration

A useful synthesis of rare 1,2-disubstituted ferrocenylalkyl amines with (S(Fc),S) configuration has been achieved in a sequential one-pot methodology from (S)-p-tolylsulfinylferrocene.