Organic Letters
Organic Letters
5 years ago

Asymmetric and Site-Selective [3 + 2]-Annulations for the Synthesis of High-Value Bicyclic Lactams

Asymmetric and Site-Selective [3 + 2]-Annulations for the Synthesis of High-Value Bicyclic Lactams
Dimitris Kalaitzakis, Manolis Sofiadis, Konstantinos Daskalakis, Myron Triantafyllakis, Georgios Vassilikogiannakis
Asymmetric and site-selective formal [3 + 2]-annulations of γ-alkyl-β,γ-unsaturated γ-lactams with α,β-unsaturated aldehydes have been developed. These organocatalysed transformations yield high value enantioenriched bicyclic γ-lactams with up to four new stereocenters (sometimes including a quarternary carbon). The overall transformation starts from simple and readily accessible furans and oversees a rapid, controlled, and dramatic enhancement in 3D complexity.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.8b00076

DOI: 10.1021/acs.orglett.8b00076

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