Access to Enantioenriched Organosilanes from Enals and β‐Silyl Enones: Carbene Organocatalysis. Issue 17 (15th March 2018)

• Record Type: Journal Article
• Authors: Zhang, Yuxia; Huang, Jie; Guo, Yingying; Li, Lin; Fu, Zhenqian; Huang, Wei
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 17(2018)
• Page Start: 4594
• Page End: 4598
• Publication Date: 2018-03-15
• Subjects: cyclizations -- lactones -- N-heterocyclic carbenes -- organocatalysis -- silanes; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201800483
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Herein, an efficient route to enantioenriched organosilanes, containing two consecutive stereogenic centers, from enals and β‐silyl enones under carbene organocatalysis is described. Under mild reaction conditions, this transition‐metal‐free strategy exhibits a broad substrate scope, and excellent diastereo‐ and enantioselectivity. Abstract : Bearing down : A carbene‐enabled formal [4+2] annulation of enals with β‐silyl enones under mild reaction conditions leads to a diverse set of enantioenriched organosilanes bearing two contiguous stereocenters. This reaction is a transition‐metal‐free strategy and the products are isolated in good yields with excellent diastereo‐ and enantioselectivities. NHC=N‐heterocyclic carbene.