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Synlett 2011(14): 1987-1992  
DOI: 10.1055/s-0030-1261171
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Nickel-Catalyzed [2+2+2] Cycloaddition of Enynes and Arynes

David A. Candito, Mark Lautens*
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada
e-Mail: mlautens@chem.utoronto.ca;
Further Information

Publication History

Received 30 May 2011
Publication Date:
10 August 2011 (online)

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Abstract

Examples of stereoselective reactions of aryne intermediates are rare in the literature. A stereoselective nickel-catalyzed [2+2+2] cycloaddition of 1,6-enynes with aryne intermediates is reported. Excellent stereoselectivities were observed when a substituent is adjacent to the olefin moiety resulting in trans- stereochemistry in the products. This reaction is capable of generating much complexity from simple and readily available starting materials. Furthermore, the products possess a synthetic handle which poises them for further modifications.

Key words

nickel-catalyzed - arynes - diastereoselective - 1,6-enynes - [2+2+2] cycloaddition

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