共 28 条
Ionic liquids/H2O systems for the reaction of epoxides with NaN3:: a new protocol for the synthesis of 2-azidoalcohols
被引:45
作者:

Yadav, JS
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机构:
Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India

Reddy, BVS
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机构:
Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India

Jyothirmai, B
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Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India

Murty, MSR
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Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India
机构:
[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India
关键词:
ionic liquids (ILs);
oxiranes;
azidoalcohols;
D O I:
10.1016/j.tetlet.2005.07.074
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
Oxiranes undergo ring opening rapidly with sodium azide in a [bmim]BF4/H2O or [bmim]PF6/H2O (2: 1) solvent system, under mild and neutral reaction conditions to afford the corresponding 2-azidoalcohols in high to quantitative yields. The remarkable features of this procedure are improved yields, enhanced reaction rates, high regioselectivity and ease of recyclability of ionic liquids (ILs). The recovered ionic liquid can be reused for four to five times but with gradual decrease in activity. (c) 2005 Published by Elsevier Ltd.
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页码:6559 / 6562
页数:4
相关论文
共 28 条
[1]
1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis
[J].
Ager, DJ
;
Prakash, I
;
Schaad, DR
.
CHEMICAL REVIEWS,
1996, 96 (02)
:835-875

Ager, DJ
论文数: 0 引用数: 0
h-index: 0
机构:
MONSANTO CO, NUTRASWEET KELCO UNIT, MT PROSPECT, IL 60056 USA MONSANTO CO, NUTRASWEET KELCO UNIT, MT PROSPECT, IL 60056 USA

Prakash, I
论文数: 0 引用数: 0
h-index: 0
机构:
MONSANTO CO, NUTRASWEET KELCO UNIT, MT PROSPECT, IL 60056 USA MONSANTO CO, NUTRASWEET KELCO UNIT, MT PROSPECT, IL 60056 USA

Schaad, DR
论文数: 0 引用数: 0
h-index: 0
机构:
MONSANTO CO, NUTRASWEET KELCO UNIT, MT PROSPECT, IL 60056 USA MONSANTO CO, NUTRASWEET KELCO UNIT, MT PROSPECT, IL 60056 USA
[2]
TRICHOGIN-A-IV, AN 11-RESIDUE LIPOPEPTAIBOL FROM TRICHODERMA-LONGIBRACHIATUM
[J].
AUVINGUETTE, C
;
REBUFFAT, S
;
PRIGENT, Y
;
BODO, B
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1992, 114 (06)
:2170-2174

AUVINGUETTE, C
论文数: 0 引用数: 0
h-index: 0
机构: MUSEUM NATL HIST NAT,CHIM LAB,CNRS,URA 401,GDR 964,63 RUE BUFFON,F-75231 PARIS 05,FRANCE

REBUFFAT, S
论文数: 0 引用数: 0
h-index: 0
机构: MUSEUM NATL HIST NAT,CHIM LAB,CNRS,URA 401,GDR 964,63 RUE BUFFON,F-75231 PARIS 05,FRANCE

PRIGENT, Y
论文数: 0 引用数: 0
h-index: 0
机构: MUSEUM NATL HIST NAT,CHIM LAB,CNRS,URA 401,GDR 964,63 RUE BUFFON,F-75231 PARIS 05,FRANCE

BODO, B
论文数: 0 引用数: 0
h-index: 0
机构: MUSEUM NATL HIST NAT,CHIM LAB,CNRS,URA 401,GDR 964,63 RUE BUFFON,F-75231 PARIS 05,FRANCE
[3]
Regio- and stereoselective ring opening of 2,3-epoxyalcohols with diethylaluminium azide
[J].
Benedetti, F
;
Berti, F
;
Norbedo, S
.
TETRAHEDRON LETTERS,
1998, 39 (43)
:7971-7974

论文数: 引用数:
h-index:
机构:

论文数: 引用数:
h-index:
机构:

Norbedo, S
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Trieste, Dipartimento Sci Chim, I-34127 Trieste, Italy Univ Trieste, Dipartimento Sci Chim, I-34127 Trieste, Italy
[4]
Highly regioselective ring opening of epoxides using NaN3:: a short and efficient synthesis of (-)-cytoxazone
[J].
Boruwa, J
;
Borah, JC
;
Kalita, B
;
Barua, NC
.
TETRAHEDRON LETTERS,
2004, 45 (39)
:7355-7358

Boruwa, J
论文数: 0 引用数: 0
h-index: 0
机构:
CSIR, Reg Res Lab, Nat Prod Chem Div, Jorhat 785006, Assam, India CSIR, Reg Res Lab, Nat Prod Chem Div, Jorhat 785006, Assam, India

Borah, JC
论文数: 0 引用数: 0
h-index: 0
机构:
CSIR, Reg Res Lab, Nat Prod Chem Div, Jorhat 785006, Assam, India CSIR, Reg Res Lab, Nat Prod Chem Div, Jorhat 785006, Assam, India

Kalita, B
论文数: 0 引用数: 0
h-index: 0
机构:
CSIR, Reg Res Lab, Nat Prod Chem Div, Jorhat 785006, Assam, India CSIR, Reg Res Lab, Nat Prod Chem Div, Jorhat 785006, Assam, India

Barua, NC
论文数: 0 引用数: 0
h-index: 0
机构:
CSIR, Reg Res Lab, Nat Prod Chem Div, Jorhat 785006, Assam, India CSIR, Reg Res Lab, Nat Prod Chem Div, Jorhat 785006, Assam, India
[5]
TI(O-I-PR)4-MEDIATED NUCLEOPHILIC OPENINGS OF 2,3-EPOXY ALCOHOLS - A MILD PROCEDURE FOR REGIOSELECTIVE RING-OPENING
[J].
CARON, M
;
SHARPLESS, KB
.
JOURNAL OF ORGANIC CHEMISTRY,
1985, 50 (09)
:1557-1560

CARON, M
论文数: 0 引用数: 0
h-index: 0
机构:
MIT,DEPT CHEM,CAMBRIDGE,MA 02139 MIT,DEPT CHEM,CAMBRIDGE,MA 02139

SHARPLESS, KB
论文数: 0 引用数: 0
h-index: 0
机构:
MIT,DEPT CHEM,CAMBRIDGE,MA 02139 MIT,DEPT CHEM,CAMBRIDGE,MA 02139
[6]
EFFICIENT METAL SALT CATALYZED AZIDOLYSIS OF EPOXIDES WITH SODIUM-AZIDE IN ACETONITRILE
[J].
CHINI, M
;
CROTTI, P
;
MACCHIA, F
.
TETRAHEDRON LETTERS,
1990, 31 (39)
:5641-5644

CHINI, M
论文数: 0 引用数: 0
h-index: 0
机构:
UNIV PISA,DIPARTIMENTO CHIM BIOORGAN,VIA BONANNO 33,I-56100 PISA,ITALY UNIV PISA,DIPARTIMENTO CHIM BIOORGAN,VIA BONANNO 33,I-56100 PISA,ITALY

CROTTI, P
论文数: 0 引用数: 0
h-index: 0
机构:
UNIV PISA,DIPARTIMENTO CHIM BIOORGAN,VIA BONANNO 33,I-56100 PISA,ITALY UNIV PISA,DIPARTIMENTO CHIM BIOORGAN,VIA BONANNO 33,I-56100 PISA,ITALY

MACCHIA, F
论文数: 0 引用数: 0
h-index: 0
机构:
UNIV PISA,DIPARTIMENTO CHIM BIOORGAN,VIA BONANNO 33,I-56100 PISA,ITALY UNIV PISA,DIPARTIMENTO CHIM BIOORGAN,VIA BONANNO 33,I-56100 PISA,ITALY
[7]
REGIOCHEMICAL CONTROL OF THE RING-OPENING OF 1,2-EPOXIDES BY MEANS OF CHELATING PROCESSES .3. AMINOLYSIS AND AZIDOLYSIS OF THE CIS-OXIDES AND TRANS-OXIDES DERIVED FROM 4-(BENZYLOXY)CYCLOHEXENE
[J].
CHINI, M
;
CROTTI, P
;
FLIPPIN, LA
;
MACCHIA, F
.
JOURNAL OF ORGANIC CHEMISTRY,
1991, 56 (25)
:7043-7048

CHINI, M
论文数: 0 引用数: 0
h-index: 0
机构: UNIV PISA,DIPARTIMENTO CHIM BIOORGAN,VIA BONANNO 33,I-56126 PISA,ITALY

CROTTI, P
论文数: 0 引用数: 0
h-index: 0
机构:
UNIV PISA,DIPARTIMENTO CHIM BIOORGAN,VIA BONANNO 33,I-56126 PISA,ITALY UNIV PISA,DIPARTIMENTO CHIM BIOORGAN,VIA BONANNO 33,I-56126 PISA,ITALY

FLIPPIN, LA
论文数: 0 引用数: 0
h-index: 0
机构: UNIV PISA,DIPARTIMENTO CHIM BIOORGAN,VIA BONANNO 33,I-56126 PISA,ITALY

MACCHIA, F
论文数: 0 引用数: 0
h-index: 0
机构: UNIV PISA,DIPARTIMENTO CHIM BIOORGAN,VIA BONANNO 33,I-56126 PISA,ITALY
[8]
SYNTHESIS OF COMPOUNDS ACTIVE AGAINST HIV .2. PREPARATION OF SOME 2',3'-DIDEOXY-6'-FLUOROCARBOCYCLIC NUCLEOSIDES
[J].
COE, DM
;
MYERS, PL
;
PARRY, DM
;
ROBERTS, SM
;
STORER, R
.
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS,
1990, (02)
:151-153

COE, DM
论文数: 0 引用数: 0
h-index: 0
机构:
GLAXO GRP RES LTD,DEPT MICROBIOL CHEM,GREENFORD UB6 0HE,MIDDX,ENGLAND GLAXO GRP RES LTD,DEPT MICROBIOL CHEM,GREENFORD UB6 0HE,MIDDX,ENGLAND

MYERS, PL
论文数: 0 引用数: 0
h-index: 0
机构:
GLAXO GRP RES LTD,DEPT MICROBIOL CHEM,GREENFORD UB6 0HE,MIDDX,ENGLAND GLAXO GRP RES LTD,DEPT MICROBIOL CHEM,GREENFORD UB6 0HE,MIDDX,ENGLAND

PARRY, DM
论文数: 0 引用数: 0
h-index: 0
机构:
GLAXO GRP RES LTD,DEPT MICROBIOL CHEM,GREENFORD UB6 0HE,MIDDX,ENGLAND GLAXO GRP RES LTD,DEPT MICROBIOL CHEM,GREENFORD UB6 0HE,MIDDX,ENGLAND

ROBERTS, SM
论文数: 0 引用数: 0
h-index: 0
机构:
GLAXO GRP RES LTD,DEPT MICROBIOL CHEM,GREENFORD UB6 0HE,MIDDX,ENGLAND GLAXO GRP RES LTD,DEPT MICROBIOL CHEM,GREENFORD UB6 0HE,MIDDX,ENGLAND

STORER, R
论文数: 0 引用数: 0
h-index: 0
机构:
GLAXO GRP RES LTD,DEPT MICROBIOL CHEM,GREENFORD UB6 0HE,MIDDX,ENGLAND GLAXO GRP RES LTD,DEPT MICROBIOL CHEM,GREENFORD UB6 0HE,MIDDX,ENGLAND
[9]
A STABLE AND EASILY PREPARED CATALYST FOR THE ENANTIOSELECTIVE REDUCTION OF KETONES - APPLICATIONS TO MULTISTEP SYNTHESES
[J].
COREY, EJ
;
BAKSHI, RK
;
SHIBATA, S
;
CHEN, CP
;
SINGH, VK
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1987, 109 (25)
:7925-7926

COREY, EJ
论文数: 0 引用数: 0
h-index: 0

BAKSHI, RK
论文数: 0 引用数: 0
h-index: 0

SHIBATA, S
论文数: 0 引用数: 0
h-index: 0

CHEN, CP
论文数: 0 引用数: 0
h-index: 0

SINGH, VK
论文数: 0 引用数: 0
h-index: 0
[10]
LIPASE-CATALYZED RESOLUTION OF ACYCLIC AMINO ALCOHOL PRECURSORS
[J].
FOELSCHE, E
;
HICKEL, A
;
HONIG, H
;
SEUFERWASSERTHAL, P
.
JOURNAL OF ORGANIC CHEMISTRY,
1990, 55 (06)
:1749-1753

FOELSCHE, E
论文数: 0 引用数: 0
h-index: 0
机构:
GRAZ UNIV TECHNOL,INST ORGAN CHEM,A-8010 GRAZ,AUSTRIA GRAZ UNIV TECHNOL,INST ORGAN CHEM,A-8010 GRAZ,AUSTRIA

HICKEL, A
论文数: 0 引用数: 0
h-index: 0
机构:
GRAZ UNIV TECHNOL,INST ORGAN CHEM,A-8010 GRAZ,AUSTRIA GRAZ UNIV TECHNOL,INST ORGAN CHEM,A-8010 GRAZ,AUSTRIA

HONIG, H
论文数: 0 引用数: 0
h-index: 0
机构:
GRAZ UNIV TECHNOL,INST ORGAN CHEM,A-8010 GRAZ,AUSTRIA GRAZ UNIV TECHNOL,INST ORGAN CHEM,A-8010 GRAZ,AUSTRIA

SEUFERWASSERTHAL, P
论文数: 0 引用数: 0
h-index: 0
机构:
GRAZ UNIV TECHNOL,INST ORGAN CHEM,A-8010 GRAZ,AUSTRIA GRAZ UNIV TECHNOL,INST ORGAN CHEM,A-8010 GRAZ,AUSTRIA