Synthesis and reactivity of a stable crystalline diastereomerically pure trifluoromethanesulfinic acid derivative:(S)-(−)-1-trifluoromethylsulfinyl-(R)-4-phenyloxazolidin-2- …

VD Romanenko, C Thoumazet, V Lavallo…

Index: Romanenko, Vadim D.; Thoumazet, Claire; Lavallo, Vincent; Tham, Fook S.; Bertrand, Guy Chemical Communications, 2003 , # 14 p. 1680 - 1681

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Abstract

Efficient synthesis of the title compound, the first diastereomerically pure trifluoromethanesulfinic acid derivative (8), has been achieved by direct trifluoromethanesulfinylation of the lithiated (4R)-(−)-4-phenyloxazolidin-2-one; in contrast to the reaction between CF3S (O) Cl and (1R, 2S, 5R)-(−)-menthol which occurs with low stereoselectivity (< 10% de), 8 affords the O-menthyl trifluoromethanesulfinate derivative ...