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

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

doi:10.1016/S0957-4166(99)00183-4

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

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

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

22 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 language	English
Pages (from-to)	1795-1802
Number of pages	8
Journal	Tetrahedron Asymmetry
Volume	10
Issue number	9
DOIs	https://doi.org/10.1016/S0957-4166(99)00183-4
State	Published - 7 May 1999

Bibliographical note

Funding Information:
This research was supported by a grant from the Korea Institute of Science and Technology.

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title = "Novel phosphinobioxazines as chiral ligands in palladium-catalyzed enantioselective allylic substitution",

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.",

author = "Lee, {Sang Gi} and Lee, {So Ha} and Song, {Choong Eui} and Chung, {Bong Young}",

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T1 - Novel phosphinobioxazines as chiral ligands in palladium-catalyzed enantioselective allylic substitution

AU - Lee, Sang Gi

AU - Lee, So Ha

AU - Song, Choong Eui

AU - Chung, Bong Young

N1 - Funding Information: This research was supported by a grant from the Korea Institute of Science and Technology.

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N2 - 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.

AB - 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.

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

Abstract

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