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

Novel C 2-symmetric chiral (4 S,4′ S)-bisphosphinobioxazine 2a, a six-membered analog of (4 S,4 S′)-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...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 1999-05, Vol.10 (9), p.1795-1802
Main Authors: Lee, Sang-gi, Lee, So Ha, Song, Choong Eui, Chung, Bong Young
Format: Article
Language:English
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Summary:Novel C 2-symmetric chiral (4 S,4′ S)-bisphosphinobioxazine 2a, a six-membered analog of (4 S,4 S′)-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. C 2-Symmetric bisphosphinobioxazine 2a exhibited moderate enantioselectivities (63–84% ee) whereas excellent enantioselectivities (94–95% ee) were observed with monophosphinobioxazine 2b.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(99)00183-4