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Reaction of the Carbanions of 2-(Alkylthio)thiolane 1-Oxides with Oxiranes (1999)

Schuler, Barbara ; Adiwidjaja, Gunadi ; Voss, Jürgen

Weinheim : Wiley-Blackwell

Liebigs Annalen 1999 (1999), S. 1481-1488

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ISSN: 1434-193X

Keywords: Thiolane 1-oxides ; Carbanions ; Oxiranes ; Asymmetric synthesis ; X-ray structure ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: -Carbanions of the 2-(alkylthio)thiolane 1-oxides 1 and 2 are generated and subjected to reaction with the epoxides 3-5. The resulting carbinols 6-11 are formed with high α diastereoselectivity, which is explained by a stabilization of the trans configuration of the carbanions in the activated complex. A minor γ stereoselectivity is also observed in case of the reactions with 4 and 5. The pure enantiomers (1S,2S,2′S)-9a and (1R,2R,2′S)-11b were obtained from 2 and (S)-4 or (R)-5, respectively, and their configurations were proved by X-ray structural analyses.

Additional Material: 2 Ill.

Type of Medium: Electronic Resource

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