通过金催化的环丙烯环化异构化反应合成 3-氧杂和 3-氮杂双环[4.1.0]庚烷。
Synthesis of 3-oxa- and 3-azabicyclo[4.1.0]heptanes by gold-catalyzed cycloisomerization of cyclopropenes.
机构信息
Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
出版信息
Org Lett. 2010 Sep 17;12(18):4144-7. doi: 10.1021/ol101741f.
PMID:20726564
Abstract
Allyl 3,3-dimethylcyclopropenylcarbinyl ethers or sulfonamides undergo gold-catalyzed cycloisomerization leading to 5-isopropylidene-3-oxa- and 3-azabicyclo[4.1.0]heptanes in excellent yields and with high diastereoselectivities. These reactions constitute the first examples of intramolecular cyclopropanation of an alkene by a gold carbene generated by electrophilic ring opening of a cyclopropene in the presence of gold(I) chloride.
摘要
烯丙基 3,3-二甲基环丙基甲醚或磺酰胺在金催化下发生环异构化反应，以高产率和高非对映选择性得到 5-异丙叉基-3-氧杂和 3-氮杂双环[4.1.0]庚烷。这些反应是首例在金（I）氯化物存在下，通过环丙烯的亲电开环生成的金卡宾对烯烃进行分子内环丙烷化的反应。
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