Benzofulvenes in Trienamine Catalysis: Stereoselective Spiroindene Synthesis.

Autor: Donslund BS; Department of Chemistry, Aarhus University, Langelandsgade 140, 8000, Aarhus C, Denmark., Nielsen RP; Department of Chemistry, Aarhus University, Langelandsgade 140, 8000, Aarhus C, Denmark., Mønsted SM; Department of Chemistry, Aarhus University, Langelandsgade 140, 8000, Aarhus C, Denmark., Jørgensen KA; Department of Chemistry, Aarhus University, Langelandsgade 140, 8000, Aarhus C, Denmark. kaj@chem.au.dk.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2016 Sep 05; Vol. 55 (37), pp. 11124-8. Date of Electronic Publication: 2016 Jul 06.
DOI: 10.1002/anie.201605079
Abstrakt: The asymmetric formation of spiroindenes containing up to four contiguous stereocenters from the reaction of benzofulvenes with 2,4-dienals through trienamine catalysis is described. The benzofulvene core was found to be an excellent starting point for the synthesis of interesting spiroindenes through a formal cycloaddition pathway. The reaction was mediated by a diphenylprolinol silyl ether catalyst, and a diverse array of spiroindenes were obtained in high yields with excellent stereoselectivity. An attractive feature of the developed system is the possibility to diversify the product scaffold significantly by further manipulation of the chiral spiroindenes. Thus, three intramolecular ring-closing reactions following the organocatalytic step resulted in highly complex polycyclic systems.
(© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
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