Synthesis and characterization of new amine-imine ligands based on trans-2,5-disubstituted pyrrolidines

James A. Sweet; Jennifer M. Cavallari; William A. Price; Joseph W. Ziller; Dominic V. McGrath

doi:10.1016/S0957-4166(96)00511-3

Synthesis and characterization of new amine-imine ligands based on trans-2,5-disubstituted pyrrolidines

James A. Sweet
, Jennifer M. Cavallari
, William A. Price
, Joseph W. Ziller
, Dominic V. McGrath

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

41 Scopus citations

Abstract

We present a modular synthesis of a new class of chiral N,N-chelating ligands containing the C₂-symmetric trans-2,5-disubstituted pyrrolidine moiety linked to a pyridine ring. (-)-2-[(2R,5R)-2,5-Dimethylpyrrolidin-1-ylmethyl]pyridine (11, (R,R)-MePMP), (-)-2-[2((2R,5R)-2,5-dimethylpyrrolidin- (12, (R,R)-MePEP), and (+)-2-[(2R,5R)-2,5-diphenylpyrrolidin-1-ylmethyl]pyridine (13, (R,R)-PhPMP) have been prepared. The X-ray structure of the (Λ³-allyl)Pd complex of (R,R)-MePMP (11) is reported.

Original language	English (US)
Pages (from-to)	207-211
Number of pages	5
Journal	Tetrahedron Asymmetry
Volume	8
Issue number	2
DOIs	https://doi.org/10.1016/S0957-4166(96)00511-3
State	Published - Jan 23 1997
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1016/S0957-4166(96)00511-3

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@article{9a7e47c9bdd447b68e2c9712b595b095,

title = "Synthesis and characterization of new amine-imine ligands based on trans-2,5-disubstituted pyrrolidines",

abstract = "We present a modular synthesis of a new class of chiral N,N-chelating ligands containing the C2-symmetric trans-2,5-disubstituted pyrrolidine moiety linked to a pyridine ring. (-)-2-[(2R,5R)-2,5-Dimethylpyrrolidin-1-ylmethyl]pyridine (11, (R,R)-MePMP), (-)-2-[2((2R,5R)-2,5-dimethylpyrrolidin- (12, (R,R)-MePEP), and (+)-2-[(2R,5R)-2,5-diphenylpyrrolidin-1-ylmethyl]pyridine (13, (R,R)-PhPMP) have been prepared. The X-ray structure of the (Λ3-allyl)Pd complex of (R,R)-MePMP (11) is reported.",

author = "Sweet, \{James A.\} and Cavallari, \{Jennifer M.\} and Price, \{William A.\} and Ziller, \{Joseph W.\} and McGrath, \{Dominic V.\}",

note = "Funding Information: We are grateful to Per-Ola Norrby and Mark Burk for helpful discussions. Acknowledgement is made to the donors of The Petroleum Research Fund, administered by the ACS, and the University of Connecticut Research Foundation for support of this research. J.M.C. was the recipient of a Pfizer Summer Undergraduate Research Fellowship, for which she is grateful.",

year = "1997",

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doi = "10.1016/S0957-4166(96)00511-3",

language = "English (US)",

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pages = "207--211",

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T1 - Synthesis and characterization of new amine-imine ligands based on trans-2,5-disubstituted pyrrolidines

AU - Sweet, James A.

AU - Cavallari, Jennifer M.

AU - Price, William A.

AU - Ziller, Joseph W.

AU - McGrath, Dominic V.

N1 - Funding Information: We are grateful to Per-Ola Norrby and Mark Burk for helpful discussions. Acknowledgement is made to the donors of The Petroleum Research Fund, administered by the ACS, and the University of Connecticut Research Foundation for support of this research. J.M.C. was the recipient of a Pfizer Summer Undergraduate Research Fellowship, for which she is grateful.

PY - 1997/1/23

Y1 - 1997/1/23

N2 - We present a modular synthesis of a new class of chiral N,N-chelating ligands containing the C2-symmetric trans-2,5-disubstituted pyrrolidine moiety linked to a pyridine ring. (-)-2-[(2R,5R)-2,5-Dimethylpyrrolidin-1-ylmethyl]pyridine (11, (R,R)-MePMP), (-)-2-[2((2R,5R)-2,5-dimethylpyrrolidin- (12, (R,R)-MePEP), and (+)-2-[(2R,5R)-2,5-diphenylpyrrolidin-1-ylmethyl]pyridine (13, (R,R)-PhPMP) have been prepared. The X-ray structure of the (Λ3-allyl)Pd complex of (R,R)-MePMP (11) is reported.

AB - We present a modular synthesis of a new class of chiral N,N-chelating ligands containing the C2-symmetric trans-2,5-disubstituted pyrrolidine moiety linked to a pyridine ring. (-)-2-[(2R,5R)-2,5-Dimethylpyrrolidin-1-ylmethyl]pyridine (11, (R,R)-MePMP), (-)-2-[2((2R,5R)-2,5-dimethylpyrrolidin- (12, (R,R)-MePEP), and (+)-2-[(2R,5R)-2,5-diphenylpyrrolidin-1-ylmethyl]pyridine (13, (R,R)-PhPMP) have been prepared. The X-ray structure of the (Λ3-allyl)Pd complex of (R,R)-MePMP (11) is reported.

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DO - 10.1016/S0957-4166(96)00511-3

M3 - Article

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SN - 0957-4166

VL - 8

SP - 207

EP - 211

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

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Synthesis and characterization of new amine-imine ligands based on trans-2,5-disubstituted pyrrolidines

Abstract

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