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Synthesis of Boc-protected bicycloproline.

ABSTRACT: 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.

SUBMITTER: Ranatunga S 

PROVIDER: S-EPMC2808134 | biostudies-literature | 2009 May

REPOSITORIES: biostudies-literature

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Synthesis of Boc-protected bicycloproline.

Ranatunga Sujeewa S   Del Valle Juan R JR  

Tetrahedron letters 20090501 21

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. ...[more]