1379829-57-8Relevant articles and documents
Intriguing Electrophilic Reactivity of Donor–Acceptor Cyclopropanes: Experimental and Theoretical Studies
Dousset, Maxime,Parrain, Jean-Luc,Chouraqui, Ga?lle
, p. 5238 - 5245 (2017)
A new reactivity of donor–acceptor cyclopropanes (DACs) has been highlighted and, for the first time, we report that they could formally behave as nucleophiles and be functionalized at their C3 position. The donor–acceptor cyclopropane acts as a formal nucleophilic synthetic equivalent of a 1,2-zwitterion and could be described as an umpolung synthon. A highly substituted lactone is reached, and even more impressive is the formation of four stereogenic centers with complete control of their relative configuration. Both experimental and computational studies were performed to provide an overall picture of the mechanism.
Highly diastereoselective construction of fused carbocycles from cyclopropane-1,1-dicarboxylates and cyclic enol silyl ethers: Scope, Mechanism, and origin of diastereoselectivity
Qu, Jian-Ping,Liang, Yong,Xu, Hao,Sun, Xiu-Li,Yu, Zhi-Xiang,Tang, Yong
, p. 2196 - 2201 (2012/04/10)
Cyclopropane rings true: By selecting the appropriate substituents on the ester and silyl groups, fused cyclopentane derivatives with multiple contiguous stereocenters can be synthesized with excellent diastereoselectivity through CuII/bisoxazoline-catalyzed intermolecular [3+2] cycloaddition reactions of cyclopropane-1,1-dicarboxylates and cyclic enol silyl ethers (see scheme). Copyright
