The Journal of Organic Chemistry

Convenient Syntheses of Chiral Cyclic Sulfinates (Sultines) from Unsaturated Alcohols

CM Marson, PR Giles

文献索引：Marson, Charles M.; Giles, Paul R. Journal of Organic Chemistry, 1995 , vol. 60, # 24 p. 8067 - 8073

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被引用次数: 13

摘要

The reaction of unsaturated alcohols with N-sulfinyl-p-toluenesulfonamide(TsNSO) is shown to lead stereoselectively to chiral cyclic or bicyclic sulfinates (sultines). The reactions occur at ambient temperatures and afford a general route to 6-and E-sultines which are notable for their crystallinity and thermal stability. These studies confirm the preservation of stereochemical integrity of the carbon atom a to the oxygen atom in the sultine ring. Some ...