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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