Synthesis and reactivity of a stable crystalline diastereomerically pure trifluoromethanesulfinic acid derivative: (S)-(−)-1-trifluoromethylsulfinyl-(R)-4-phenyloxazolidin-2-one
Literature Information
Publication Date
2003-06-09
DOI
10.1039/B303574C
Impact Factor
6.222
Authors
Vadim D. Romanenko, Claire Thoumazet, Vincent Lavallo, Fook S. Tham, Guy Bertrand
View Original
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 in >98% de.
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Source Journal
Chemical Communications
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4.7%
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Recommended Compounds
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4-[(2-{2-[2-(2-Aminoethoxy)ethoxy]ethoxy}ethyl)amino]-2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione
CAS Number:
2093416-31-8
Molecular Formula:
C21H28N4O7
![[5-fluoro-2-(morpholine-4-carbonyl)phenyl]boronic acid structure](https://static.chemtradehub.com/structs/121/1217501-26-2-505c.webp "[5-fluoro-2-(morpholine-4-carbonyl)phenyl]boronic acid structure")
[5-fluoro-2-(morpholine-4-carbonyl)phenyl]boronic acid
CAS Number:
1217501-26-2
Molecular Formula:
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