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Synlett 1993; 1993(11): 831-833
DOI: 10.1055/s-1993-22622
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Stannanes in Synthesis: The Generation of Promoter-Incorporated o-Quinodimethanes

H. Sano* , K. Kawata, M. Kosugi
  • *Department of Chemistry, Gunma University, Kiryu, Gunma 376, Japan
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Publication Date:
19 March 2002 (online)

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A new and convenient method for the generation of o-quinodimethane intermediate 2 is described. Precursors of o-quinodimethanes bearing a variety of substituents 1 could be prepared in only three steps. The precursors, o-alkenylbenzyltributylstannanes 1, reacted with dienophiles in the presence of electrophiles at room temperature to give cycloadducts 3 in high yields. The cycloadditions proceeded with high stereoselectivity.

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