Brønsted Base Catalyzed One-Pot Synthesis of Stereodefined Six-Member Carbocycles Featuring Transient Trienolates and a Key Intramolecular 1,6-Addition.

Authors :: Olaizola O
Iriarte I
Zanella G
Gómez-Bengoa E
Ganboa I
Oiarbide M
Palomo C
Source :: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2019 Oct 01; Vol. 58 (40), pp. 14250-14254. Date of Electronic Publication: 2019 Aug 30.
Publication Year :: 2019
Abstract: A catalyst-driven one-pot reaction sequence is developed for the enantio- and diastereoselective synthesis of tetrasubstituted cyclohexenes from simple unsaturated ketones or thioesters. The method involves a tertiary amine/squaramide-catalyzed α-selective addition of transiently generated trienolates to nitroolefins, subsequent base-catalyzed double bond isomerization, and an intramolecular (vinylogous) 1,6-addition reaction, a rare key carbocyclization step that proceeded with essentially perfect stereocontrol.<br /> (© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

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