A Route to 2‐Alkenyl‐3‐( tert ‐butyldiphenylsilyl)amines and Application to the Construction of a Tricyclic Ring System | Zendy

Yadav Veejendra K. | Zendy; Narhe Bharat D. | Zendy; Kumar Kamlesh | Zendy; Hulikal Vijaykumar | Zendy

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A Route to 2‐Alkenyl‐3‐( tert ‐butyldiphenylsilyl)amines and Application to the Construction of a Tricyclic Ring System

Author(s) -

Yadav Veejendra K.,

Narhe Bharat D.,

Kumar Kamlesh,

Hulikal Vijaykumar

Publication year - 2013

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201300319

Subject(s) - tosyl , chemistry , deprotonation , cleavage (geology) , ring (chemistry) , bond cleavage , ion , medicinal chemistry , carbenium ion , stereochemistry , organic chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering

N ‐ Tosyl 3,3 ‐ dialkyl ‐ 2 ‐ ( tert ‐ butyldiphenylsilylmethyl)azetidines rearrange smoothly into the corresponding 2 ‐ alkenyl ‐ 3 ‐ ( tert ‐ butyldiphenylsilyl)amines upon exposure to BF 3 · OEt 2 in CH 2 Cl 2 . The reaction involves sequential σ C–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 σ C–N bond cleavage, which leads to high configurational control at the tert ‐butyldiphenylsilylmethyl ‐ bearing carbon atom in the product.

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