Synthesis of Boc-protected bicycloproline.
The synthesis of a highly constrained quaternary carbocyclic α-amino acid, (+)-N-Boc-bicycloproline, has been achieved starting from sodium cyclopentadienylide. Key steps include a rhodium-catalyzed nitrenoid C-H insertion to install the tert-alkylamine and a ring-closing metathesis reaction to form the pyrrolidine ring.
Ranatunga
Sujeewa
S
Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, NM 88003.
Del Valle
Juan R
JR