Highly enantioselective intramolecular cyanoamidation: (+)-horsfiline, (-)-coerulescine, and (-)-esermethole

Venkata Jaganmohan Reddy, Christopher J. Douglas

Research output: Contribution to journalArticlepeer-review

49 Scopus citations

Abstract

(Figure Presented) The first asymmetric cyanoamidation with synthetically useful enantioselectivlty (ee up to 99%) to produce 3,3-disubstltuted oxindoles Is reported. Palladium catalysts with chi ral phosphoramldite ligands activate the cyanoformamide C-CN bond, which is subsequently functionalized with a tethered alkene to give all-carbon quaternary stereocenters. The use of the N,N-(i-Pr)2 derivative of octahydro-MonoPhos allowed the production of oxindoles with high enantioselectivlties. Cyanoformamides bearing free N-H groups are now tolerated, potentially allowing protecting-group-free synthesis. Oxindole products of cyanoamidation are rapidly transformed into (+)-horsfiline, (-)-coerulescine, and (-)-esermethole.

Original languageEnglish (US)
Pages (from-to)952-955
Number of pages4
JournalOrganic Letters
Volume12
Issue number5
DOIs
StatePublished - Mar 5 2010

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