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- Title
A Route to 2-Alkenyl-3-( tert-butyldiphenylsilyl)amines and Application to the Construction of a Tricyclic Ring System.
- Authors
Yadav, Veejendra K.; Narhe, Bharat D.; Kumar, Kamlesh; Hulikal, Vijaykumar
- Abstract
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 the N -tosyl-aminomethyl group, and deprotonation of the resultant tert -carbenium ions. For the instance in which the carbenium ion formed from migration of the N -tosyl-aminomethyl group is highly stable by virtue of being, for example, tertiary as well as benzylic, the migration takes place in sync with σC-N bond cleavage, which leads to high configurational control at the tert-butyldiphenylsilylmethyl -bearing carbon atom in the product.
- Subjects
ALKENYLATION; AMINES; SCISSION (Chemistry); HYPOGLYCIN A; CARBON
- Publication
European Journal of Organic Chemistry, 2013, Vol 2013, Issue 19, p4163
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201300319