A Route to 2‐Alkenyl‐3‐(tert‐butyldiphenylsilyl)amines and Application to the Construction of a Tricyclic Ring System
作者： Veejendra K. Yadav , Bharat D. Narhe , Kamlesh Kumar , Vijaykumar Hulikal
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摘要: N-Tosyl 3,3-dialkyl-2-(tert-butyldiphenylsilylmethyl)azetidines rearrange smoothly into the corresponding 2-alkenyl-3-(tert-butyldiphenylsilyl)amines upon exposure to BF3·OEt2 in CH2Cl2. The reaction involves sequential σC–N bond cleavage, 1,2-migration of N-tosyl-aminomethyl group, and deprotonation resultant tert-carbenium ions. For instance which carbenium ion formed from migration group is highly stable by virtue being, for example, tertiary as well benzylic, takes place sync with leads high configurational control at tert-butyldiphenylsilylmethyl-bearing carbon atom product.
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