Stereoselective 6π-Electron Electrocyclic Ring Closures

doi:10.1055/s-0030-1259473

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Synfacts 2011(3): 0299-0299
DOI: 10.1055/s-0030-1259473

Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions

Stereoselective 6π-Electron Electrocyclic Ring Closures

Contributor(s): Mark Lautens, David A. Candito
R. Hayashi, M. C. Walton, R. P. Hsung*, J. H. Schwab, X. Yu
University of Wisconsin-Madison, USA

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Publication History

Publication Date:
16 February 2011 (online)

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Significance

Identifying highly stereoselective manifolds for 6π-electrocyclization of 1,3,5-hexa-trienes remains a challenge in organic synthesis. A diastereoselective electrocyclization of 2-halo-3-amidotrienes is described in which the substituent acts to relay the chiral information to the remote 6-position.