Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2006(7): 0726-0726
DOI: 10.1055/s-2006-941909
DOI: 10.1055/s-2006-941909
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York
Asymmetric Diels-Alder Reaction Catalyzed by a Chiral Diammonium Salt
A. Sakakura, K. Suzuki, K. Nakano, K. Ishihara*
Nagoya University, Japan
Further Information
Publication History
Publication Date:
22 June 2006 (online)
Significance
A new organocatalytic asymmetric Diels-Alder reaction has been reported. The diammonium salt of chiral 1,1′-binaphthyl-2,2′-diamine and Tf2NH catalyzes the reaction of dienes 1 with α-acyloxyacroleins 2 to give adducts of type 3 in good yields, enantioselectivities and diastereoselectivities. Both cyclic as well as acyclic precursors 1 can be used. In addition, a transition state, based on NMR spectroscopy and X-ray crystal structure analysis, to explain the observed relative and absolute configuration is proposed.