Confined Acid-Catalyzed Asymmetric Carbonyl鈥揈ne Cyclization
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- 作者：Luping Liu ; Markus Leutzsch ; Yiying Zheng ; M. Wasim Alachraf ; Walter Thiel ; Benjamin List
- 刊名：Journal of the American Chemical Society
- 出版年：2015
- 出版时间：October 21, 2015
- 年：2015
- 卷：137
- 期：41
- 页码：13268-13271
- 全文大小：397K
- ISSN：1520-5126
文摘
A highly enantioselective Br酶nsted acid catalyzed intramolecular carbonyl鈥揺ne reaction of olefinic aldehydes has been developed. Using a confined imidodiphosphate catalyst, the reaction delivers diverse trans-3,4-disubstituted carbo- and heterocyclic five-membered rings in high yields and with good to excellent diastereo- and enantioselectivities. ESI-MS, NMR, and DFT mechanistic studies reveal that the reaction proceeds via a stepwise pathway involving a novel covalent intermediate.