Cinchona Alkaloid/Sulfinyl Chloride Combinations: Enantioselective Sulfinylating Agents of Alcohols

We report a novel approach to asymmetric sulfinylation reactions based on a cinchona alkaloid/sulfinyl chloride combination that acts as the first asymmetric sulfinylating agents of achiral alcohols. Both enantiomers of arenesulfinates are obtained with up to 99% ee. The significantly high enantiose...

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Veröffentlicht in:	Journal of the American Chemical Society 2005-02, Vol.127 (5), p.1374-1375
Hauptverfasser:	Shibata, Norio, Matsunaga, Mitsuharu, Nakagawa, Masaya, Fukuzumi, Takeo, Nakamura, Shuichi, Toru, Takeshi
Format:	Artikel
Sprache:	eng
Schlagworte:	Alcohols - chemistry Chemical reactivity Chemistry Cinchona Alkaloids - chemistry Exact sciences and technology Organic chemistry Reactivity and mechanisms Stereoisomerism Sulfinic Acids - chemical synthesis Sulfinic Acids - chemistry
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Beschreibung
Zusammenfassung:	We report a novel approach to asymmetric sulfinylation reactions based on a cinchona alkaloid/sulfinyl chloride combination that acts as the first asymmetric sulfinylating agents of achiral alcohols. Both enantiomers of arenesulfinates are obtained with up to 99% ee. The significantly high enantioselectivity observed in this case could be explained by dynamic kinetic resolution.
ISSN:	0002-7863 1520-5126
DOI:	10.1021/ja0430189