Gold(I)-Catalyzed Desymmetrization of 1,4-Dienes by an Enantioselective Tandem Alkoxylation/Claisen Rearrangement.

Authors :: Wu H
Zi W
Li G
Lu H
Toste FD
Source :: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2015 Jul 13; Vol. 54 (29), pp. 8529-32. Date of Electronic Publication: 2015 Jun 01.
Publication Year :: 2015
Abstract: An enantioselective alkoxylation/Claisen rearrangement reaction was achieved by a strategic desymmetrization of 1,4-dienes under the catalysis of (S)-DTBM-Segphos(AuCl)2/AgBF4. This reaction system was highly selective for the formation of 3,3-rearrangement products, providing cycloheptenes with various substitutions in good yield and good to excellent enantioselectivity. This transformation was further extended to bicyclic ring substrates, providing the opportunity to easily assemble 5,6- and 6,7-fused ring systems.<br /> (© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Subjects :: Catalysis
Cycloheptanes chemistry
Polyenes chemical synthesis
Stereoisomerism
Cycloheptanes chemical synthesis
Gold chemistry
Polyenes chemistry

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