共 18 条
Zinc triflate-bis-oxazoline complexes as chiral catalysts:: enantioselective reduction of α-alkoxy-ketones with catecholborane
被引:44
作者:

Bandini, M
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机构:
Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

Cozzi, PG
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机构:
Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

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Umani-Ronchi, A
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机构:
Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
机构:
[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
关键词:
asymmetric reactions;
catalysis;
ketones;
reduction;
D O I:
10.1016/S0040-4039(99)02339-4
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
A new methodology for the catalytic enantioselective reduction of oc-alkoxy-ketones is described. The procedure employes Zn(OTf)(2)-bis-oxazoline complexes (8-10 mol%) as catalysts and catecholborane as the reducing agent. The reaction, carried out in CH2Cl2 at 0 degrees C, affords the alpha-alkoxy-alcohols in high yields and with good enantioselectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.
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页码:1601 / 1605
页数:5
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共 18 条
[1]
Enantioselective reduction of ketones with triethoxysilane catalyzed by chiral bis-oxazoline titanium complexes
[J].
Bandini, M
;
Cozzi, PG
;
Negro, L
;
Umani-Ronchi, A
.
CHEMICAL COMMUNICATIONS,
1999, (01)
:39-40

Bandini, M
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

Cozzi, PG
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

Negro, L
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

Umani-Ronchi, A
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
[2]
Stereoselective synthesis of α,α-disubstituted amines by a sequential nucleophilic addition to O-protected cyanohydrins
[J].
Charette, AB
;
Gagnon, A
.
TETRAHEDRON-ASYMMETRY,
1999, 10 (10)
:1961-1968

Charette, AB
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada

Gagnon, A
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
[3]
Facile synthesis of terminal 1,2-diols with high optical purity via oxazaborolidine-catalyzed asymmetric borane reduction
[J].
Cho, BT
;
Chun, YS
.
JOURNAL OF ORGANIC CHEMISTRY,
1998, 63 (15)
:5280-5282

Cho, BT
论文数: 0 引用数: 0
h-index: 0
机构:
Hallym Univ, Dept Chem, Kangwondo 200702, South Korea Hallym Univ, Dept Chem, Kangwondo 200702, South Korea

Chun, YS
论文数: 0 引用数: 0
h-index: 0
机构:
Hallym Univ, Dept Chem, Kangwondo 200702, South Korea Hallym Univ, Dept Chem, Kangwondo 200702, South Korea
[4]
A practical method for synthesis of terminal 1,2-diols in high enantiomeric excess via oxazaborolidine-catalyzed asymmetric reduction
[J].
Cho, BT
;
Chun, YS
.
TETRAHEDRON-ASYMMETRY,
1999, 10 (10)
:1843-1846

Cho, BT
论文数: 0 引用数: 0
h-index: 0
机构:
Hallym Univ, Dept Chem, Chunchon 200702, Kangwondo, South Korea Hallym Univ, Dept Chem, Chunchon 200702, Kangwondo, South Korea

Chun, YS
论文数: 0 引用数: 0
h-index: 0
机构:
Hallym Univ, Dept Chem, Chunchon 200702, Kangwondo, South Korea Hallym Univ, Dept Chem, Chunchon 200702, Kangwondo, South Korea
[5]
A CATALYTIC ENANTIOSELECTIVE SYNTHESIS OF DENOPAMINE, A USEFUL DRUG FOR CONGESTIVE-HEART-FAILURE
[J].
COREY, EJ
;
LINK, JO
.
JOURNAL OF ORGANIC CHEMISTRY,
1991, 56 (01)
:442-444

COREY, EJ
论文数: 0 引用数: 0
h-index: 0
机构: Department of Chemistry, Harvard University, Cambridge

LINK, JO
论文数: 0 引用数: 0
h-index: 0
机构: Department of Chemistry, Harvard University, Cambridge
[6]
Catalytic enantioselective Michael additions to unsaturated ester derivatives using chiral copper(II) Lewis acid complexes
[J].
Evans, DA
;
Willis, MC
;
Johnston, JN
.
ORGANIC LETTERS,
1999, 1 (06)
:865-868

Evans, DA
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

Willis, MC
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

Johnston, JN
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
[7]
C2-symmetric copper(II) complexes as chiral Lewis acids.: Scope and mechanism of catalytic enantioselective aldol additions of enolsilanes to (benzyloxy)acetaldehyde
[J].
Evans, DA
;
Kozlowski, MC
;
Murry, JA
;
Burgey, CS
;
Campos, KR
;
Connell, BT
;
Staples, RJ
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1999, 121 (04)
:669-685

Evans, DA
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

Kozlowski, MC
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

Murry, JA
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

Burgey, CS
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

Campos, KR
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

Connell, BT
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

Staples, RJ
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
[8]
Bis(oxazoline) and bis(oxazolinyl)pyridine copper complexes as enantioselective Diels-Alder catalysts: Reaction scope and synthetic applications
[J].
Evans, DA
;
Barnes, DM
;
Johnson, JS
;
Lectka, R
;
von Matt, P
;
Miller, SJ
;
Murry, JA
;
Norcross, RD
;
Shaughnessy, EA
;
Campos, KR
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1999, 121 (33)
:7582-7594

Evans, DA
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

Barnes, DM
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

Johnson, JS
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

Lectka, R
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

von Matt, P
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

Miller, SJ
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

Murry, JA
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

Norcross, RD
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

Shaughnessy, EA
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

Campos, KR
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
[9]
An improved procedure for the preparation of 2,2-bis[2-[4(S)-tert-butyl-1,3-oxazolinyl]]propane [(S,S)-tert-butylbis(oxazoline)] and derived copper(II) complexes
[J].
Evans, DA
;
Peterson, GS
;
Johnson, JS
;
Barnes, DM
;
Campos, KR
;
Woerpel, KA
.
JOURNAL OF ORGANIC CHEMISTRY,
1998, 63 (13)
:4541-4544

Evans, DA
论文数: 0 引用数: 0
h-index: 0
机构:
MIT, Dept Chem & Biol Chem, Cambridge, MA 02139 USA MIT, Dept Chem & Biol Chem, Cambridge, MA 02139 USA

Peterson, GS
论文数: 0 引用数: 0
h-index: 0
机构:
MIT, Dept Chem & Biol Chem, Cambridge, MA 02139 USA MIT, Dept Chem & Biol Chem, Cambridge, MA 02139 USA

Johnson, JS
论文数: 0 引用数: 0
h-index: 0
机构:
MIT, Dept Chem & Biol Chem, Cambridge, MA 02139 USA MIT, Dept Chem & Biol Chem, Cambridge, MA 02139 USA

Barnes, DM
论文数: 0 引用数: 0
h-index: 0
机构:
MIT, Dept Chem & Biol Chem, Cambridge, MA 02139 USA MIT, Dept Chem & Biol Chem, Cambridge, MA 02139 USA

Campos, KR
论文数: 0 引用数: 0
h-index: 0
机构:
MIT, Dept Chem & Biol Chem, Cambridge, MA 02139 USA MIT, Dept Chem & Biol Chem, Cambridge, MA 02139 USA

Woerpel, KA
论文数: 0 引用数: 0
h-index: 0
机构:
MIT, Dept Chem & Biol Chem, Cambridge, MA 02139 USA MIT, Dept Chem & Biol Chem, Cambridge, MA 02139 USA
[10]
C2-symmetric chiral bis(oxazoline)-metal complexes in catalytic asymmetric synthesis
[J].
Ghosh, AK
;
Packiarajan, M
;
Cappiello, J
.
TETRAHEDRON-ASYMMETRY,
1998, 9 (01)
:1-45

Ghosh, AK
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Illinois, Dept Chem, Chicago, IL 60607 USA Univ Illinois, Dept Chem, Chicago, IL 60607 USA

Packiarajan, M
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Illinois, Dept Chem, Chicago, IL 60607 USA Univ Illinois, Dept Chem, Chicago, IL 60607 USA

Cappiello, J
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Illinois, Dept Chem, Chicago, IL 60607 USA Univ Illinois, Dept Chem, Chicago, IL 60607 USA