Synthesis of homologated binaphthyl N,P-ligands for Pd-catalyzed asymmetric allylic alkylation

Kyoung Hoon Kim; Chan Kyu Jeong; Do Hoon Kim; Deok Chan Ha

doi:10.1016/j.tetasy.2006.06.013

Synthesis of homologated binaphthyl N,P-ligands for Pd-catalyzed asymmetric allylic alkylation

Kyoung Hoon Kim, Chan Kyu Jeong, Do Hoon Kim, Deok Chan Ha

College of Science

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

8 Citations (Scopus)

Abstract

2-Pyrrolidinylmethyl-2′-diphenylphosphino-1,1′-binaphthyl has been found to be a highly reactive and enantioselective N,P-ligand in the palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenylpropen-2-yl acetate with dimethyl malonate. This axially chiral binaphthyl-based homologated N,P-ligand can be conveniently prepared from enantiomerically pure binaphthol using a five-step reaction sequence, and provides for efficient asymmetric catalysis using the chirality of the binaphthyl skeleton alone.

Original language	English
Pages (from-to)	1688-1692
Number of pages	5
Journal	Tetrahedron Asymmetry
Volume	17
Issue number	11
DOIs	https://doi.org/10.1016/j.tetasy.2006.06.013
Publication status	Published - 2006 Jul 17

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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@article{9cd3cfc0a7ac435ab762cd902450e8d6,

title = "Synthesis of homologated binaphthyl N,P-ligands for Pd-catalyzed asymmetric allylic alkylation",

abstract = "2-Pyrrolidinylmethyl-2′-diphenylphosphino-1,1′-binaphthyl has been found to be a highly reactive and enantioselective N,P-ligand in the palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenylpropen-2-yl acetate with dimethyl malonate. This axially chiral binaphthyl-based homologated N,P-ligand can be conveniently prepared from enantiomerically pure binaphthol using a five-step reaction sequence, and provides for efficient asymmetric catalysis using the chirality of the binaphthyl skeleton alone.",

author = "Kim, {Kyoung Hoon} and Jeong, {Chan Kyu} and Kim, {Do Hoon} and Ha, {Deok Chan}",

note = "Funding Information: This work was financially supported by Korea Research Foundation Grant (KRF-2003-015-C00358).",

year = "2006",

month = jul,

day = "17",

doi = "10.1016/j.tetasy.2006.06.013",

language = "English",

volume = "17",

pages = "1688--1692",

journal = "Tetrahedron Asymmetry",

issn = "0957-4166",

publisher = "Elsevier Limited",

number = "11",

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TY - JOUR

T1 - Synthesis of homologated binaphthyl N,P-ligands for Pd-catalyzed asymmetric allylic alkylation

AU - Kim, Kyoung Hoon

AU - Jeong, Chan Kyu

AU - Kim, Do Hoon

AU - Ha, Deok Chan

N1 - Funding Information: This work was financially supported by Korea Research Foundation Grant (KRF-2003-015-C00358).

PY - 2006/7/17

Y1 - 2006/7/17

N2 - 2-Pyrrolidinylmethyl-2′-diphenylphosphino-1,1′-binaphthyl has been found to be a highly reactive and enantioselective N,P-ligand in the palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenylpropen-2-yl acetate with dimethyl malonate. This axially chiral binaphthyl-based homologated N,P-ligand can be conveniently prepared from enantiomerically pure binaphthol using a five-step reaction sequence, and provides for efficient asymmetric catalysis using the chirality of the binaphthyl skeleton alone.

AB - 2-Pyrrolidinylmethyl-2′-diphenylphosphino-1,1′-binaphthyl has been found to be a highly reactive and enantioselective N,P-ligand in the palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenylpropen-2-yl acetate with dimethyl malonate. This axially chiral binaphthyl-based homologated N,P-ligand can be conveniently prepared from enantiomerically pure binaphthol using a five-step reaction sequence, and provides for efficient asymmetric catalysis using the chirality of the binaphthyl skeleton alone.

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U2 - 10.1016/j.tetasy.2006.06.013

DO - 10.1016/j.tetasy.2006.06.013

M3 - Article

AN - SCOPUS:33745847789

VL - 17

SP - 1688

EP - 1692

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

SN - 0957-4166

IS - 11

ER -

Synthesis of homologated binaphthyl N,P-ligands for Pd-catalyzed asymmetric allylic alkylation

Abstract

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