Templated Assembly of Chiral Medium-Sized Cyclic Ethers via 8-endo-trig Nucleophilic Cyclization of Cyclopropenes
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- 作者：Pavel Ryabchuk ; Jonathon P. Matheny ; Marina Rubina ; Michael Rubin
- 刊名：Organic Letters
- 出版年：2016
- 出版时间：December 16, 2016
- 年：2016
- 卷：18
- 期：24
- 页码：6272-6275
- 全文大小：370K
- ISSN：1523-7052
文摘
An efficient approach toward enantioenriched eight-membered heterocycles via the intramolecular formal substitution of bromocyclopropanes with oxygen-based nucleophiles has been developed. The reaction proceeds via a reactive cyclopropene intermediate, which undergoes a rapid 8-endo-trig cyclization affording cis-fused [6.1.0] bicyclic products exclusively. The quaternary chiral center in the cyclopropene governs the configuration of the other two stereocenters in the final product.