Novel phosphinobioxazines as chiral ligands in palladium-catalyzed enantioselective allylic substitution

Sang Gi Lee, So Ha Lee, Choong Eui Song, Bong Young Chung

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

Novel C2-symmetric chiral (4S,4'S)-bisphosphinobioxazine 2a, a six- membered analog of (4S,4S')bisphosphinobioxazoline (Phos-Biox, 1), and monophosphinobioxazine 2b have been synthesized and used as chiral ligands for Pd-catalyzed asymmetric allylic substitutions of rac-1,3-diphenyl-2- propenyl acetate with dimethyl malonate. C2-Symmetric bisphosphinobioxazine 2a exhibited moderate enantioselectivities (63-84% ee) whereas excellent enantioselectivities (94-95% ee) were observed with monophosphinobioxazine 2b.

Original languageEnglish
Pages (from-to)1795-1802
Number of pages8
JournalTetrahedron Asymmetry
Volume10
Issue number9
DOIs
StatePublished - 7 May 1999

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