Nitrogen Nucleophiles in Intramolecular Michael Reactions of Nitrosoalkenes
Open Access
Author:
Wang, Tony Lingguang
Area of Honors:
Chemistry
Degree:
Bachelor of Science
Document Type:
Thesis
Thesis Supervisors:
Steven M Weinreb, Thesis Supervisor Steven M Weinreb, Thesis Supervisor Przemyslaw Maslak, Thesis Honors Advisor Katherine Mary Masters, Faculty Reader
Keywords:
nitrogen nucleophiles michael reaction nitrosoalkene vinylnitroso
Abstract:
Novel methodology to effect an intramolecular 1,4 conjugate addition of a nitrogen nucleophile to a nitrosoalkene has been developed. Previous studies in the Weinreb lab have shown that vinylnitroso species generated from the corresponding α-chloro-O-silyloximes react with tethered nucleophiles in an intramolecular Michael reaction to produce a variety of carbocyclic and heterocyclic products. Recently, a new and more efficient Diels-Alder based pathway for synthesizing the precursor to access bridged azaheterocycle 63 was tested. The bridged ring ketone 64 was successfully synthesized from 2-methoxybutadiene (56) in eight steps in 13% overall yield using a key vinylnitroso conjugate addition, and studies to extend the methodology to other systems are currently being investigated in the Weinreb group.
