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.