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Synfacts 2008(10): 1073-1073  
DOI: 10.1055/s-2008-1078237
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Platinum-Catalyzed Intramolecular Vinylthiolation and Vinylselenation

Contributor(s): Mark Lautens, Praew Thansandote
M. Toyofuku, S. Fujiwara*, T. Shin-ike, H. Kuniyasu, N. Kambe*
Osaka University and Osaka Dental University, Japan
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Publication History

Publication Date:
22 September 2008 (online)

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Significance

A novel platinum(0)-catalyzed inter- and intramolecular vinylthiolation and vinylselenation of alkynes is reported to give highly conjugated six-membered lactams. The scope is good and explores substitution effects on the alkyne, the nitrogen protecting group, and the heteroatom. For TMS-substituted alkynes, the crude mixture of the initial lactam product can be treated with a mild base for in situ removal of the TMS group.