Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 21, Pages 8491-8496Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo801687v
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Funding
- National Natural Science Foundation of China [20772116]
- Program of NCET [1060551]
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Cycloadditions of alkynyl ketones with N-tosylimines catalyzed by Lewis bases to synthesize azetidines and pyrrolidines were systematically described. In the reaction of alkynyl ketones with N-tosylimines catalyzed by Bu3P at room temperature in toluene, highly functionalized pyrrolidines were formed in good to excellent yields. When DMAP was used in place of Bu3P as catalyst to facilitate the cycloaddition, completely substituted azetidines were produced in moderate to good yields in CH2Cl2. Both cyclization reactions proceeded smoothly with complete stereoselectivity. The scope and limitations of these cycloadditon reactions were also investigated.
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