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

Dimitris Kalaitzakis | Zendy; Manolis Sofiadis | Zendy; Myron Triantafyllakis | Zendy; Konstantinos S. Daskalakis | Zendy; Georgios Vassilikogiannakis | Zendy

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

Author(s) -

Dimitris Kalaitzakis,

Manolis Sofiadis,

Myron Triantafyllakis,

Konstantinos S. Daskalakis,

Georgios Vassilikogiannakis

Publication year - 2018

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.8b00076

Subject(s) - stereocenter , bicyclic molecule , chemistry , yield (engineering) , alkyl , combinatorial chemistry , stereochemistry , lactam , value (mathematics) , enantioselective synthesis , catalysis , organic chemistry , mathematics , statistics , materials science , metallurgy

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.

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