Enantioselective Diels-Alder reactions: Room temperature bis(oxazoline)-zinc, -magnesium, and -copper triflate catalysts

James M. Takacs; Edward C. Lawson; Michael J. Reno; Mark A. Youngman; David A. Quincy

doi:10.1016/S0957-4166(97)00322-4

Enantioselective Diels-Alder reactions: Room temperature bis(oxazoline)-zinc, -magnesium, and -copper triflate catalysts

James M. Takacs
, Edward C. Lawson
, Michael J. Reno
, Mark A. Youngman
, David A. Quincy

Cooperative Programs for the Advancement of Earth System Science

University of Nebraska-Lincoln

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

53 Scopus citations

Abstract

A series of chiral bis(oxazoline) ligands, differing in the length of the chain connecting the chiral oxazoline subunits and in the nature of the substituent at the chiral center, were examined in the room temperature Zn(OTf)₂, Mg(OTf)₂ and Cu(OTf)₂ catalyzed reaction of N-crotonyloxazolidinone with cyclopentadiene. A 1,4-bis(oxazoline) ligand proved best for Zn(OTf)₂ and afforded product consistent with reaction via an octahedral model, while 1,3-bis(oxazoline) ligands were best for Mg(OTf)₂ and Cu(OTf)₂.

Original language	English
Pages (from-to)	3073-3078
Number of pages	6
Journal	Tetrahedron Asymmetry
Volume	8
Issue number	18
DOIs	https://doi.org/10.1016/S0957-4166(97)00322-4
State	Published - Sep 25 1997

Access to Document

10.1016/S0957-4166(97)00322-4

Cite this

@article{2299146dcb14412c8dfe09c97f92d97e,

title = "Enantioselective Diels-Alder reactions: Room temperature bis(oxazoline)-zinc, -magnesium, and -copper triflate catalysts",

abstract = "A series of chiral bis(oxazoline) ligands, differing in the length of the chain connecting the chiral oxazoline subunits and in the nature of the substituent at the chiral center, were examined in the room temperature Zn(OTf)2, Mg(OTf)2 and Cu(OTf)2 catalyzed reaction of N-crotonyloxazolidinone with cyclopentadiene. A 1,4-bis(oxazoline) ligand proved best for Zn(OTf)2 and afforded product consistent with reaction via an octahedral model, while 1,3-bis(oxazoline) ligands were best for Mg(OTf)2 and Cu(OTf)2.",

author = "Takacs, \{James M.\} and Lawson, \{Edward C.\} and Reno, \{Michael J.\} and Youngman, \{Mark A.\} and Quincy, \{David A.\}",

year = "1997",

month = sep,

day = "25",

doi = "10.1016/S0957-4166(97)00322-4",

language = "English",

volume = "8",

pages = "3073--3078",

journal = "Tetrahedron Asymmetry",

issn = "0957-4166",

publisher = "Elsevier Ltd",

number = "18",

}

TY - JOUR

T1 - Enantioselective Diels-Alder reactions

T2 - Room temperature bis(oxazoline)-zinc, -magnesium, and -copper triflate catalysts

AU - Takacs, James M.

AU - Lawson, Edward C.

AU - Reno, Michael J.

AU - Youngman, Mark A.

AU - Quincy, David A.

PY - 1997/9/25

Y1 - 1997/9/25

N2 - A series of chiral bis(oxazoline) ligands, differing in the length of the chain connecting the chiral oxazoline subunits and in the nature of the substituent at the chiral center, were examined in the room temperature Zn(OTf)2, Mg(OTf)2 and Cu(OTf)2 catalyzed reaction of N-crotonyloxazolidinone with cyclopentadiene. A 1,4-bis(oxazoline) ligand proved best for Zn(OTf)2 and afforded product consistent with reaction via an octahedral model, while 1,3-bis(oxazoline) ligands were best for Mg(OTf)2 and Cu(OTf)2.

AB - A series of chiral bis(oxazoline) ligands, differing in the length of the chain connecting the chiral oxazoline subunits and in the nature of the substituent at the chiral center, were examined in the room temperature Zn(OTf)2, Mg(OTf)2 and Cu(OTf)2 catalyzed reaction of N-crotonyloxazolidinone with cyclopentadiene. A 1,4-bis(oxazoline) ligand proved best for Zn(OTf)2 and afforded product consistent with reaction via an octahedral model, while 1,3-bis(oxazoline) ligands were best for Mg(OTf)2 and Cu(OTf)2.

UR - https://www.scopus.com/pages/publications/0030884898

U2 - 10.1016/S0957-4166(97)00322-4

DO - 10.1016/S0957-4166(97)00322-4

M3 - Article

AN - SCOPUS:0030884898

SN - 0957-4166

VL - 8

SP - 3073

EP - 3078

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 18

ER -

Enantioselective Diels-Alder reactions: Room temperature bis(oxazoline)-zinc, -magnesium, and -copper triflate catalysts

Abstract

Access to Document

Other files and links

Fingerprint

Cite this