Remarkable effects of lone pair-lone pair interactions on the extremely stereoselective [2+ 2] cycloaddition of azidoketene to chiral 3-imino-. beta.-lactams

I Ojima, K Nakahashi, SM Brandstadter…

文献索引：Ojima, Iwao; Nakahashi, Kazuaki; Brandstadter, Stephan M.; Hatanaka, Naoto Journal of the American Chemical Society, 1987 , vol. 109, # 6 p. 1798 - 1805

全文：HTML全文

被引用次数: 37

摘要

Abstract: The stereoselective [2+ 21 cycloadditions of azidoketene to cis-3-imino-~-lactams 1, 2, and 3, trans-3-imino-P-lactam 4, and cis-3-iminoazetidine 5 were carried out. It was found that the reactions of 1, 2, and 3 prded with> 99.5% stereoselectivity to give bis-P- lactams 9, 14, and 19, respectively. The reaction of 4 gave a bis-P-lactam 20 with 62% de, and the reaction of 5 gave a P-lactamazetidine 21 with 32% de inducing the asymmetry in ...