The proposal describes the development of a mild and efficient method for the catalytic asymmetric synthesis of vinyl chromans. The chroman motif is present in numerous small molecules of biological importance and the current methods available to access these substrates are limited. The SN2'allylic substitution chemistry of trichloroacetimidates using a tethered phenol nucleophile will be examined using chiral cobalt oxazoline palladium(ll) catalysts. An efficient and convergent method to access a variety of key cyclization substrates will be developed. The scope of functional groups and substitution patterns compatible with this system will be explored. A variety of heterocycles with important biological activity may also be synthesized using this chemistry. This methodology will allow easy access to a broader range of biologically active small molecules and their analogues. This proposal describes the development of a general method to access biologically important small molecules in a selective manner. This methodology will be beneficial to the synthetic community because a vast number of small molecules and their analogues will be readily available and their biological activity can be explored.
| Cannon, Jeffrey S; Olson, Angela C; Overman, Larry E et al. (2012) Palladium(II)-catalyzed enantioselective synthesis of 2-vinyl oxygen heterocycles. J Org Chem 77:1961-73 |
| Olson, Angela C; Overman, Larry E; Sneddon, Helen F et al. (2009) Catalytic Asymmetric Synthesis of Branched Chiral Allylic Phenyl Ethers from (E)-Allylic Alcohols. Adv Synth Catal 351:3186-3192 |
