Brønsted base-catalyzed annulation of allyl ketones and alkynyl 1, 2-diketones. Issue 34 (9th April 2018)

• Record Type: Journal Article
• Authors: Kong, Xiangwen; Song, Jinshuai; Liu, Jian; Meng, Miao; Yang, Shuang; Zeng, Min; Zhan, Xinyue; Li, Chunsen; Fang, Xinqiang
• Is Part Of: Chemical communications. Volume 54:Issue 34(2018)
• Page Start: 4266
• Page End: 4269
• Publication Date: 2018-04-09
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c8cc01020j
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : The Cs2 CO3 -catalyzed reaction of allyl ketones and alkynyl 1, 2-diketones affords a series of 2-acyloxycyclopent-3-enones under mild conditions. A unique α-selective addition/aldol reaction/C–C bond cleavage mechanism was proposed and supported by DFT calculations. Abstract : The discovery of new reaction modes mediated by easily available substrates is an important research topic in organic synthesis. Allyl ketones and related compounds have been demonstrated to undergo γ- or α-selective additions to different electrophiles. We disclose here the Brønsted base-catalyzed reaction of allyl ketones and alkynyl 1, 2-diketones, which undergo a unique α-selective addition/intramolecular aldol-type annulation/C–C bond cleavage process, and a series of 2-acyloxycyclopent-3-enones can be obtained under very mild conditions.