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Synfacts 2007(1): 0061-0061  
DOI: 10.1055/s-2006-955737
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Chemodivergent Formation of Furanones and Piperidines

Contributor(s): Mark Lautens, Frédéric Ménard
S. Muthusamy*, J. Krishnamurthi, E. Suresh
Bharathidasan University, Tiruchirappalli and Central Salt & Marine Chemicals Research Institute, Bhavnagar, India
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Publication History

Publication Date:
15 December 2006 (online)

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Significance

The method is useful to synthesize highly functionalized furanones and piperidines. With the appropriate Lewis acid, it was possible to chemoselectively ring-open the bicyclic system under similar conditions. The common [2.2.1] oxa-brided piperidone was prepared by a Rh(II)-cata­lyzed 1,3-dipolar cycloaddition (S. Muthusamy,J. Krishnamurthi, E. Suresh Synlett 2005, 3002-3004). Importantly, the ring-opened products were obtained as single diastereoisomers. Both cis- and trans-3,4-piperidine diols 5 and 6 can be synthesized, depending on the order of addition of the reducing agents.