Synthesis of highly enantioenriched cyanohydrins by dual Lewis acid – Lewis base activation

ORGN 655

Erica Wingstrand, ericaw@kth.se1, Stina Lundgren1, Anders Hamberg2, Karl Hult2, and Christina Moberg, kimo@kth.se3. (1) Department of Organic Chemistry, KTH School of Chemical Science and Engineering, Stockholm, SE 100 44, Sweden, (2) Department of Biochemistry, AlbaNova University Center, KTH School of Biotechnology, Stockholm, SE 106 91, Sweden, (3) Department of Chemistry, KTH School of Chemical Science and Engineering, Stockholm, SE 100 44, Sweden
Enantioenriched acylated cyanohydrins serve as versatile synthons and are themselves important synthetic targets. By using our efficient catalytic dual Lewis acid – Lewis base activation system, a range of α-ketonitriles were added to both aromatic and aliphatic aldehydes affording highly enantioenriched O-acylated cyanohydrins in excellent yields. The reactions proceeded smoothly in only one step with perfect atom economy. Our recent results as well as the scope and limitations of the system will be presented together with mechanistic aspects.

 

Asymmetric Reactions and Syntheses
8:00 AM-12:00 PM, Wednesday, August 22, 2007 BCEC -- 253 A/B/C, Oral

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007