Stereocontrolled synthesis of E-homoallylic sulfides with 1, 4, 5 related chiral centres using the [2, 3] sigmatropic rearrangement of sulfonium ylides

RC Hartley, IC Richards, S Warren

文献索引：Hartley, Richard C.; Richards, Ian C.; Warren, Stuart Journal of the Chemical Society - Perkin Transactions 1, 1996 , # 4 p. 359 - 376

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被引用次数: 7

摘要

E-Homoallylic sulfides with 1, 4, 5 related chiral centres have been synthesised in a stereocontrolled way. An aldol condensation sets up the stereochemistry. Lactonisation with 1, 2 arylsulfanyl migration followed by reduction and sulfur-assisted dehydration converts the aldols stereospecifically into allylic sulfides with 1, 2 related chiral centres. Sulfonium salts are generated from the allylic sulfides at low temperature, and are deprotonated to ...