N-Heterocyclic carbene-catalyzed desymmetrization of functionalized 1,4-dienes via Stetter ReactionElectronic supplementary information (ESI) available: Experimental procedures and spectroscopic data for all new compounds. CCDC 1438493. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6cc01011c

• Main Authors: Lin, Qiqiao, Li, Yuanzhen, Das, Deb Kumar, Zhang, Guoxiang, Zhao, Zhifei, Yang, Shuang, Fang, Xinqiang
• Format: Journal Article
• Published: 03.05.2016
• ISSN: 1359-7345; 1364-548X
• DOI: 10.1039/c6cc01011c

The asymmetric desymmetrization of 1,4-dienes via chiral N-heterocyclic carbene catalyzed Stetter-type umpolung reaction was demonstrated. A variety of differently substituted dienes were tolerated very well, affording cyclic ketones with two consecutive stereogenic centers (including one quaternary carbon) in moderate to high yields and with high to excellent enantioselectivities. This work expanded both reaction types of catalytic diene desymmetrizations and substrate diversity in NHC catalyzed desymmetric transformations. The asymmetric desymmetrization of 1,4-dienes via chiral N-heterocyclic carbene catalyzed Stetter-type umpolung reaction was demonstrated.