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Synfacts 2010(8): 0924-0924  
DOI: 10.1055/s-0030-1257778
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Heterobicycles by Intramolecular Aza-Prins Reaction

Contributor(s): Mark Lautens, Stephen G. Newman
B. V. S. Reddy*, P. Borkar, P. P. Chakravarthy, J. S. Yadav, R. Gree
Indian Institute for Chemical Technology, Hyderabad, India and Université de Rennes 1, France
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Publication History

Publication Date:
22 July 2010 (online)

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Significance

Domino reactions can provide rapid access to complex products from simple starting materials. The Prins and aza-Prins reactions are two well-established domino reactions, which proceed via an intermediate oxocarbenium or iminium ion, respectively. Complimentary to their previous work on the intramolecular Prins reaction with ­epoxides (J. Org. Chem. 2010, 75, 2081), the authors utilize polyfunctional hex-3-enes as substrates for intramolecular Prins and aza-Prins reactions to synthesize complex 6,5-fused heterobicycles. In the process of the reaction, three new bonds and three new stereocenters are generated with excellent stereoselectivity.