Enantioselective N-heterocyclic carbene-catalyzed synthesis of trifluoromethyldihydropyridinones

Dong-Ling Wang; Zhi-Qin Liang; Kun-Quan Chen; De-Qun Sun; Song Ye

doi:10.1021/acs.joc.5b00232

Enantioselective N-heterocyclic carbene-catalyzed synthesis of trifluoromethyldihydropyridinones

J Org Chem. 2015 Jun 5;80(11):5900-5. doi: 10.1021/acs.joc.5b00232. Epub 2015 May 8.

Authors

Dong-Ling Wang^{1

2}, Zhi-Qin Liang², Kun-Quan Chen^{1

2}, De-Qun Sun¹, Song Ye²

Affiliations

¹ †Marine College, Shandong University at Weihai, 180 Wenhua West Road, Weihai 264209, China.
² ‡Beijing National Laboratory for Molecular Science, Key Laboratory of Molecular Recognition and Functional, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.

PMID: 25933360
DOI: 10.1021/acs.joc.5b00232

Abstract

The enantioselective N-heterocyclic carbene-catalyzed [4 + 2] cyclocondensation of α-chloroaldehydes and trifluoromethyl N-Boc azadienes was developed, giving the corresponding 3,4-disubstituted-6-trifluoromethyldihydropyridin-2(1H)-ones in good yields with exclusive cis-selectivities and excellent enantioselectivities.