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An imino Nazarov cyclization

✍ Scribed by Marcus A Tius; Chester C Chu; Raquel Nieves-Colberg

Book ID
104230275
Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
69 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

a-Aminocyclopentenones are available in a single operation from a,b-unsaturated nitriles and (methoxy)methoxyallenes. The cyclization is equivalent to an imino Nazarov reaction.

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Tri-and tetrasubstimted 1,4-dien-3-oues 1 were treated with Lewis acid in the presence of tdethylsilane, furnishing either silyl euol ethers 4 or cyclopentanunes 5 in goud yields, depending upon wt~k-up conditions. This reaction is l~resumed to occur through oxyallyl intea'mndiate 3, which undergoes