有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
3-スルホレンを利用するジエン構築とその応用
山田 幸子高山 浩明
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ジャーナル フリー

1988 年 46 巻 9 号 p. 893-908

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Recent advances in the chemistry of 3- sulfolene, 2, 5- dihydrothiophene 1, 1-dioxide, are reviewed from a view point of diene synthesis. Reaction of 3- sulfolene α- carbanion generated under a variety of basic conditions with various electrophiles followed by a stereoselective desulfonylation provides a new method for synthesizing (E) -, (E, Z) -, and (E, E) -conjugated dienes with extremely high stereoselectivity. The method is applied to the syntheses of various natural products having a conjugated diene structure. 3-Sulfolenes are used as masked dienes in the syntheses of cyclic compounds including natural products via inter- and intramolecular Diels-Alder reactions. Some other developments of the chemistry of 3-sulfolenes and its benzo analogs, benzo [c] -1, 3-dihydrothiophene 2, 2-dioxides, are briefly reviewed.

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