Reports: ND152040-ND1: Oximes as More Nucleophilic and Chiral Water
Liming Zhang, University of California, Santa Barbara
With the support of this grant, we first embarked on studying
racemic hydration of enones using various oximes. A range of structural features
are incorporated into the designed oximes to facilitate the key fragmentation
of the N-O bond upon prior oxime ether formation (Scheme 1). Unfortunately, all
of our attempts have met with little success. In some cases, the functionalized
oximes are difficult to prepared, while in other cases the oximes are not
stable under basic reaction conditions en route to the desired oxime ethers. We
also encountered difficulties in one-pot fragmentation of the N-O bond.
After much experimentation and few little encouraging
results, we are contemplating a different project, which is still in the spirit
of a new direction. I will send the request of changing project soon.