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Vinylogous Reactivity of Cyclic 2‐Enones: Organocatalysed Asymmetric Addition to 2‐Enals to Synthesize Fused Carbocycles
Author(s) -
Sofiadis Manolis,
Kalaitzakis Dimitris,
Sarris John,
Montag Tamsyn,
Vassilikogiannakis Georgios
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201901902
Subject(s) - reactivity (psychology) , chemistry , organocatalysis , stereochemistry , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , medicine , alternative medicine , pathology
A method for asymmetric and site selective annulations at the γ and γ′ positions of cyclic 2‐enones with α,β‐unsaturated aldehydes has been developed. The organocatalysed [3+3]‐annulations proceed with high levels of regio‐, diastereo‐, and enantioselectivity, affording a series of high value fused carbocycles. Further elaboration gave key lactones (both bridged and fused).