Stereocontrolled 1,3-Phosphatyloxy and 1,3-Halogen Migration Relay toward Highly Functionalized 1,3-Dienes
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- 作者：Roohollah Kazem Shiroodi ; Alexander S. Dudnik ; Vladimir Gevorgyan
- 刊名：The Journal of the American Chemical Society
- 出版年：2012
- 出版时间：April 25, 2012
- 年：2012
- 卷：134
- 期：16
- 页码：6928-6931
- 全文大小：339K
- 年卷期：v.134,no.16(April 25, 2012)
- ISSN：1520-5126
文摘
A double migratory cascade reaction of 伪-halogen-substituted propargylic phosphates to produce highly functionalized 1,3-dienes has been developed. This transformation features 1,3-phosphatyloxy group migration followed by 1,3-shifts of bromine and chlorine as well as the unprecedented 1,3-migration of iodine. The reaction is stereodivergent: (Z)-1,3-dienes are formed in the presence of a copper catalyst, whereas gold-catalyzed reactions exhibit inverted stereoselectivity, producing the corresponding E products.