Sulfinyl-Mediated Stereoselective Overman Rearrangements and Diels–Alder Cycloadditions
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- 作者：Ignacio Colomer ; Chirag Gheewala ; Carmen Simal ; Marina Velado ; Roberto Fernández de la Pradilla ; Alma Viso
- 刊名：Journal of Organic Chemistry
- 出版年：2016
- 出版时间：May 20, 2016
- 年：2016
- 卷：81
- 期：10
- 页码：4081-4097
- 全文大小：784K
- 年卷期：0
- ISSN：1520-6904
文摘
Sulfinyl trichloroacetamides are readily obtained in excellent yields through a highly stereoselective Overman rearrangement. Related bis-allylic substrates lead to amido 2-sulfinyl butadiene derivatives in excellent yields, with total chemo- and diastereoselectivity. These amido dienyl sulfoxides undergo highly selective Diels–Alder cycloadditions with N-phenylmaleimide with remarkable stereocontrol by the sulfoxide moiety.