Enantiocontrolled synthesis of 2,3,6-trisubstituted piperidines using (η3-dihydropyridinyl)molybdenum complexes as chiral scaffolds. Total synthesis of (-)-indolizidine 209B

Abstract

Enantiopure TpMo(CO)2(pyridinyl) complexes were prepared using an efficient and scalable enzymatic kinetic resolution of the precursor to the molybdenum complex. A single TpMo(CO)2(pyridinyl) complex can function as a chiral scaffold for the enantiocontrolled synthesis of either 2,3,6-cis- or 2,6-cis-3-trans-trisubstituted piperidines. The synthetic potential of this methodology was demonstrated by a total synthesis of (-)-indolizidine 209B.