New Organic Chemistry of Sulfur Dioxide

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• 作者：Pierre Vogel ; Mris Turks ; Laure Bouchez ; Dean Marković ; Adriá ; n Varela-Á ; lvarez ; José ; Á ; ngel Sordo
• 刊名：Accounts of Chemical Research
• 出版年：2007
• 出版时间：October 2007
• 年：2007
• 卷：40
• 期：10
• 页码：931 - 942
• 全文大小：360K
• 年卷期：v.40,no.10(October 2007)
• ISSN：1520-4898

文摘

Simple 1,3-dienes undergo highly stereoselective hetero-Diels–Alder additions with SO₂ at low temperature giving sultines. These reactions that are faster than the more exothermic cheletropic additions of SO₂-producing sulfolenes. This has led to the invention of a new C–C bond-forming reaction combining electron-rich dienes and alkenes with SO₂. The reaction cascade has been exploited to develop combinatorial, one-pot, four-component syntheses of polyfunctional sulfones, sulfonamides, and sulfonic esters. It also allows us to generate, in one-pot operations, enantiomerically enriched polypropionate fragments containing up to three contiguous stereogenic centers and a (E)-alkene unit. These fragments can be used directly in further C–C bond-forming reactions, such as cross-aldol condensations, thus permitting the expeditious construction of complicated natural products of biological interest (e.g., Baconipyrones, Rifamycin S, Apoptolidinone) and analogues. New ene reactions of SO₂ have also been discovered; they open new avenues to organic synthesis.