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Lewis acid-catalyzed [4+2]type cycloadditions of aldimines bearing α-hydrogens with 2-silyloxy-1,3-butadienes

✍ Scribed by Kaori Ishimaru; Yohsuke Yamamoto; Kin-ya Akiba

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
525 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

were synthesized by [4+2]type cycloaddition of chiral aldimines (5) with 2silyloxy-l,3-butadienes (3) in the presence of Lewis acids. In the cycloaddition, only two 2,6-trans isomers (chelation and nonchelation products) were observed and no cis compounds were detected regardless of the Lewis acid used. Chelation-controlled products 6b, 8b, and 9b were obtained selectively by the use of TiC14-i-PrCN and 6a was obtained with high selectivity when TMSOTf or ZnfOTf)2 was used as a Lewis acid at 4 °C, The scope of the reaction is also described.

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