Phosphine-catalyzed regiospecific allylic amination and dynamic kinetic resolution of Morita-Baylis-Hillman acetates

Chang Woo Cho, Jong Rock Kong, Michael J. Krische

Research output: Contribution to journalArticlepeer-review

195 Scopus citations

Abstract

Exposure of Morita-Baylis-Hillman (MBH) acetates to tertiary phosphine catalysts in the presence of 4,5-dichlorophthalimide enables regiospecific allylic substitution through a tandem SN2′-S N2′ mechanism. Through the use of the chiral phosphine catalyst (R)-Cl-MeO-BIPHEP, chiral racemic MBH acetate 4 is converted to the corresponding allylic amination product in 80% yield and 56% enantiomeric excess, thus establishing the feasibility of dynamic kinetic resolution.

Original languageEnglish
Pages (from-to)1337-1339
Number of pages3
JournalOrganic Letters
Volume6
Issue number8
DOIs
StatePublished - 15 Apr 2004

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