Synthesis of Planar Chiral Phosphapalladacycles byN-Acyl Amino Acid Mediated Enantioselective Palladation

M. Emin Günay, Chris Richards

Research output: Contribution to journalArticle

51 Citations (Scopus)

Abstract

Hydrolysis of scalemic trichloroacetamides Cl3CCONHCH(R)CHCH2 and allylation, or acylation with but-3-enoic acid, followed by ring-closing metathesis resulted in the formation of unsaturated pyrrolidine and piperidine building blocks. These were employed in the synthesis of (S)-coniine (R = Pr) and a formal synthesis of (+)-anisomycin (R = p-MeOC6H4). Extension of this methodology with R = CH2CHCH2 employing two ring-closing metatheses resulted in the synthesis of unsaturated quinolizidinone and indolizidinone frameworks.
Original languageEnglish
Pages (from-to)5833-5836
Number of pages4
JournalOrganometallics
Volume28
Issue number19
DOIs
Publication statusPublished - 2009

Cite this