SCOPUS 정보 검색 플랫폼

Volumn 131, Issue 3-4, 2009, Pages 432-439

Highly enantioselective organocatalytic addition of ethyl trifluoropyruvate to ketones with subzero temperature microwave activation

(2) Landge, Shainaz M a Török, Béla a

a UNIVERSITY OF MASSACHUSETTS BOSTON (United States)

Author keywords

Asymmetric synthesis; Microwave irradiation; Organocatalysis; Organofluorine; Subzero temperature

Indexed keywords

ASYMMETRIC SYNTHESIS; DIASTEREO- AND ENANTIOSELECTIVITY; ENANTIOSELECTIVE; HIGH YIELD; MICROWAVE ACTIVATION; MICROWAVE CHEMISTRY; MICROWAVE-ASSISTED; ORGANOCATALYSIS; ORGANOCATALYTIC; ORGANOFLUORINE; SUB-ZERO TEMPERATURES; SUBZERO TEMPERATURE; SYNTHONS;

CATALYSIS; ELECTRON TRANSITIONS; ENANTIOSELECTIVITY; IRRADIATION; KETONES; RATE CONSTANTS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

MICROWAVE IRRADIATION;

EID: 70349211623 PISSN: 1011372X EISSN: 1572879X Source Type: Journal
DOI: 10.1007/s10562-009-0102-0 Document Type: Article

Times cited : (24)

References (43)

1
- 0001365893
- 10.1021/ja01634a101
- J Fried EF Sabo 1954 J Am Chem Soc 7 1455 10.1021/ja01634a101
- (1954) J Am Chem Soc , vol.7 , pp. 1455
- Fried, J.¹ Sabo, E.F.²

2
- 0003481072
- V.A. Soloshonok (eds). Wiley New York
- Soloshonok VA (ed) (1999) Enantiocontrolled synthesis of fluoroorganic compounds. Stereochemical challenges and biomedicinal targets. Wiley, New York
- (1999) Enantiocontrolled Synthesis of Fluoroorganic Compounds. Stereochemical Challenges and Biomedicinal Targets

3
- 70349202742
- Asymmetric fluoroorganic chemistry
- Ramachandran PV (ed) ACS, Washington, DC
- Ramachandran PV (ed) (2001) Asymmetric fluoroorganic chemistry, ACS Symposium. Series, ACS, Washington, DC
- (2001) ACS Symposium. Series

4
- 0003961898
- T. Hiyama (eds). Springer Berlin
- Hiyama T (ed) (2001) Organofluorine compounds. Springer, Berlin
- (2001) Organofluorine Compounds

5
- 84891565619
- Wiley New York
- Kirsch P (2004) Modern fluoroorganic chemistry: synthesis, reactivity, applications. Wiley, New York
- (2004) Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications
- Kirsch, P.¹

6
- 70349224367
- Soloshonok VA (ed) ACS: Washington DC
- Soloshonok VA (ed) (2005) Fluorine-containing synthons; ACS Symposium. Series, ACS: Washington DC
- (2005) Fluorine-Containing Synthons; ACS Symposium. Series

7
- 33746318363
- Construction of asymmetric fluorinated carbon centers
- DOI 10.1002/anie.200503783
- GKS Prakash P Beier 2006 Angew Chem Int Ed 45 2172 10.1002/anie.200503783 1:CAS:528:DC%2BD28XjsFChsb8%3D (Pubitemid 44105142)
- (2006) Angewandte Chemie - International Edition , vol.45 , Issue.14 , pp. 2172-2174
- Prakash, G.K.S.¹ Beier, P.²

8
- 0031140114
- 10.1021/cr9408991 1:CAS:528:DyaK2sXisF2mu74%3D
- GKS Prakash A Yudin 1997 Chem Rev 97 757 10.1021/cr9408991 1:CAS:528:DyaK2sXisF2mu74%3D
- (1997) Chem Rev , vol.97 , pp. 757
- Prakash, G.K.S.¹ Yudin, A.²

9
- 0035793282
- Stereoselective nucleophilic trifluoromethylation of N-(tert- butylsulfinyl)imines by using trimethyl(trifluoromethyl)silane
- DOI 10.1002/1521-3773(20010202)40:3<589::AID-ANIE589>3.0.CO;2-9
- GKS Prakash M Mandal GA Olah 2001 Angew Chem Int Ed 40 589 10.1002/1521-3773(20010202)40:3<589::AID-ANIE589>3.0.CO;2-9 1:CAS:528:DC%2BD3MXhsVSqs78%3D (Pubitemid 32144472)
- (2001) Angewandte Chemie - International Edition , vol.40 , Issue.3 , pp. 589-590
- Prakash, G.K.S.¹ Mandal, M.² Olah, G.A.³

10
- 33645988190
- 10.1021/bi0601104
- M Török M Abid SC Mhadgut B Török 2006 Biochemistry 45 5377 10.1021/bi0601104
- (2006) Biochemistry , vol.45 , pp. 5377
- Török, M.¹ Abid, M.² Mhadgut, S.C.³ Török, B.⁴

11
- 0036430153
- 10.1039/b201097f 1:CAS:528:DC%2BD38Xot1KntL4%3D
- NC Yoder K Kumar 2002 Chem Soc Rev 31 335 10.1039/b201097f 1:CAS:528:DC%2BD38Xot1KntL4%3D
- (2002) Chem Soc Rev , vol.31 , pp. 335
- Yoder, N.C.¹ Kumar, K.²

12
- 34247871283
- 19F NMR-based screening and kinetic measurements
- DOI 10.1021/ja069128s
- G Papeo P Giordano MG Brasca F Buzzo D Caronni F Ciprandi N Mongelli M Veronesi A Vulpetti C Dalvit 2007 J Am Chem Soc 129 5665 10.1021/ja069128s 1:CAS:528:DC%2BD2sXjvFChtrs%3D (Pubitemid 46697656)
- (2007) Journal of the American Chemical Society , vol.129 , Issue.17 , pp. 5665-5672
- Papeo, G.¹ Giordano, P.² Brasca, M.G.³ Buzzo, F.⁴ Caronni, D.⁵ Ciprandi, F.⁶ Mongelli, N.⁷ Veronesi, M.⁸ Vulpetti, A.⁹ Dalvit, C.¹⁰

13
- 0035886887
- Enantioselective organocatalysis
- DOI 10.1002/1521-3773(20011015)40:20<3726::AID-ANIE3726>3.0.CO;2-D
- PI Dalko L Moissan 2001 Angew Chem Int Ed 40 3726 10.1002/1521- 3773(20011015)40:20<3726::AID-ANIE3726>3.0.CO;2-D 1:CAS:528: DC%2BD3MXnvFCnsL4%3D (Pubitemid 33009558)
- (2001) Angewandte Chemie - International Edition , vol.40 , Issue.20 , pp. 3726-3748
- Dalko, P.I.¹ Moisan, L.²

14
- 6044269452
- In the golden age of organocatalysis
- DOI 10.1002/anie.200400650
- PI Dalko L Moissan 2004 Angew Chem Int Ed 43 5138 10.1002/anie.200400650 1:CAS:528:DC%2BD2cXos1Kmsr4%3D (Pubitemid 39382534)
- (2004) Angewandte Chemie - International Edition , vol.43 , Issue.39 , pp. 5138-5175
- Dalko, P.I.¹ Moisan, L.²

15
- 4143136647
- 10.1021/ar030048s 1:CAS:528:DC%2BD2cXjs1ektrk%3D
- SK Tian Y Chen J Hang L Tang P McDaid L Deng 2004 Acc Chem Res 37 621 10.1021/ar030048s 1:CAS:528:DC%2BD2cXjs1ektrk%3D
- (2004) Acc Chem Res , vol.37 , pp. 621
- Tian, S.K.¹ Chen, Y.² Hang, J.³ Tang, L.⁴ McDaid, P.⁵ Deng, L.⁶

16
- 47749122232
- Wiley New York 10.1002/3527604677
- Berkessel A, Gröger H (2005) Asymmetric organocatalysis. Wiley, New York
- (2005) Asymmetric Organocatalysis
- Berkessel, A.¹ Gröger, H.²

17
- 48849094479
- 10.1002/anie.200704684 1:CAS:528:DC%2BD1cXnvFKqsLY%3D
- A Dondoni A Massi 2008 Angew Chem Int Ed 47 4638 10.1002/anie.200704684 1:CAS:528:DC%2BD1cXnvFKqsLY%3D
- (2008) Angew Chem Int Ed , vol.47 , pp. 4638
- Dondoni, A.¹ Massi, A.²

18
- 20444494428
- Direct asymmetric α-fluorination of aldehydes
- DOI 10.1002/anie.200500571
- DD Steiner N Mase CF Barbas 2005 Angew Chem Int Ed 44 3706 10.1002/anie.200500571 1:CAS:528:DC%2BD2MXlslelsLk%3D (Pubitemid 40817184)
- (2005) Angewandte Chemie - International Edition , vol.44 , Issue.24 , pp. 3706-3710
- Steiner, D.D.¹ Mase, N.² Barbas III, C.F.³

19
- 31044445377
- Enantioselective α-fluorination of carbonyl compounds: Organocatalysis or metal catalysis?
- DOI 10.1002/anie.200502425
- PM Pihko 2006 Angew Chem Int Ed 45 544 10.1002/anie.200502425 1:CAS:528:DC%2BD28XpvVeqsw%3D%3D (Pubitemid 43121443)
- (2006) Angewandte Chemie - International Edition , vol.45 , Issue.4 , pp. 544-547
- Pihko, P.M.¹

20
- 36549020091
- Cinchona-alkaloid-catalyzed enantioselective direct aldol-type reaction of oxindoles with ethyl trifluoropyruvate
- DOI 10.1002/anie.200703317
- S Ogawa N Shibata J Inagaki S Nakamura T Toru M Shira 2007 Angew Chem Int Ed 46 8666 10.1002/anie.200703317 1:CAS:528:DC%2BD2sXhtl2rsrfE (Pubitemid 350189089)
- (2007) Angewandte Chemie - International Edition , vol.46 , Issue.45 , pp. 8666-8669
- Ogawa, S.¹ Shibata, N.² Inagaki, J.³ Nakamura, S.⁴ Toru, T.⁵ Shiro, M.⁶

21
- 33645455231
- 10.1021/ja060312n 1:CAS:528:DC%2BD28XhvFamsbs%3D
- Y Wang X Liu L Deng 2006 J Am Chem Soc 128 3928 10.1021/ja060312n 1:CAS:528:DC%2BD28XhvFamsbs%3D
- (2006) J Am Chem Soc , vol.128 , pp. 3928
- Wang, Y.¹ Liu, X.² Deng, L.³

22
- 21244473265
- Dihydroxyacetone in amino acid catalyzed mannich-type reactions
- DOI 10.1002/anie.200500297
- B Westermann C Neuhaus 2005 Angew Chem Int Ed 44 4077 10.1002/anie.200500297 1:CAS:528:DC%2BD2MXmtF2gs7w%3D (Pubitemid 40886452)
- (2005) Angewandte Chemie - International Edition , vol.44 , Issue.26 , pp. 4077-4079
- Westermann, B.¹ Neuhaus, C.²

23
- 33645507049
- 10.1021/jo060064d 1:CAS:528:DC%2BD28XhtlOrsL4%3D
- B Rodriguez C Bolm 2006 J Org Chem 71 2888 10.1021/jo060064d 1:CAS:528:DC%2BD28XhtlOrsL4%3D
- (2006) J Org Chem , vol.71 , pp. 2888
- Rodriguez, B.¹ Bolm, C.²

24
- 33747205615
- Organocatalyzed asymmetric reactions via microwave activation
- DOI 10.1021/ol0614727
- S Mosse A Alexakis 2006 Org Lett 8 3577 10.1021/ol0614727 1:CAS:528:DC%2BD28XmvFaqu74%3D (Pubitemid 44238354)
- (2006) Organic Letters , vol.8 , Issue.16 , pp. 3577-3580
- Mosse, S.¹ Alexakis, A.²

25
- 33646450914
- 10.1021/ol060422z 1:CAS:528:DC%2BD28XjtVaqt7k%3D
- BK Singh P Appukkuttan S Claerhout VS Parmar EVDE Eycken 2006 Org Lett 8 1863 10.1021/ol060422z 1:CAS:528:DC%2BD28XjtVaqt7k%3D
- (2006) Org Lett , vol.8 , pp. 1863
- Singh, B.K.¹ Appukkuttan, P.² Claerhout, S.³ Parmar, V.S.⁴ Evde, E.⁵

26
- 33846986839
- Microwave-assisted asymmetric organocatalysis. A probe for nonthermal microwave effects and the concept of simultaneous cooling
- DOI 10.1021/jo0624187
- M Hosseini N Stiasni V Barbieri CO Kappe 2007 J Org Chem 72 1417 10.1021/jo0624187 1:CAS:528:DC%2BD2sXnt1KltQ%3D%3D (Pubitemid 46256848)
- (2007) Journal of Organic Chemistry , vol.72 , Issue.4 , pp. 1417-1424
- Hosseini, M.¹ Stiasni, N.² Barbieri, V.³ Kappe, C.O.⁴

27
- 0011932271
- Wiley New York
- Loupy A (2005) Microwaves in organic synthesis. Wiley, New York
- (2005) Microwaves in Organic Synthesis
- Loupy, A.¹

28
- 84949994976
- Wiley New York 10.1002/3527606556
- Kappe CO, Stadler A (2005) Microwaves in organic and medicinal chemistry. Wiley, New York
- (2005) Microwaves in Organic and Medicinal Chemistry
- Kappe, C.O.¹ Stadler, A.²

29
- 33644853780
- 10.1038/nrd1926 1:CAS:528:DC%2BD28Xmt1yqtQ%3D%3D
- CO Kappe D Dallinger 2006 Nature Rev 5 51 10.1038/nrd1926 1:CAS:528:DC%2BD28Xmt1yqtQ%3D%3D
- (2006) Nature Rev , vol.5 , pp. 51
- Kappe, C.O.¹ Dallinger, D.²

30
- 18844380223
- Highly enantioselective organocatalytic hydroxyalkylation of indoles with ethyl trifluoropyruvate
- DOI 10.1002/anie.200462877
- B Török M Abid G London J Esquibel M Török SC Mhadgut P Yan GKS Prakash 2005 Angew Chem Int Ed 44 3086 10.1002/anie.200462877 (Pubitemid 40689849)
- (2005) Angewandte Chemie - International Edition , vol.44 , Issue.20 , pp. 3086-3089
- Torok, B.¹ Abid, M.² London, G.³ Esquibel, J.⁴ Torok, M.⁵ Mhadgut, S.C.⁶ Yan, P.⁷ Prakash, G.K.S.⁸

31
- 43549085582
- 10.1021/ol703095d 1:CAS:528:DC%2BD1cXhsFeiu7c%3D
- M Abid L Teixeira B Török 2008 Org Lett 10 933 10.1021/ol703095d 1:CAS:528:DC%2BD1cXhsFeiu7c%3D
- (2008) Org Lett , vol.10 , pp. 933
- Abid, M.¹ Teixeira, L.² Török, B.³

32
- 0037043180
- Proline-catalyzed asymmetric reactions
- DOI 10.1016/S0040-4020(02)00516-1, PII S0040402002005161
- B List 2002 Tetrahedron 58 5573 10.1016/S0040-4020(02)00516-1 1:CAS:528:DC%2BD38XltVahurs%3D (Pubitemid 34722894)
- (2002) Tetrahedron , vol.58 , Issue.28 , pp. 5573-5590
- List, B.¹

33
- 4143114533
- 10.1021/ar0300468 1:CAS:528:DC%2BD2cXlsFemsb8%3D
- W Notz F Tanaka CF Barbas 2004 Acc Chem Res 37 580 10.1021/ar0300468 1:CAS:528:DC%2BD2cXlsFemsb8%3D
- (2004) Acc Chem Res , vol.37 , pp. 580
- Notz, W.¹ Tanaka, F.² Barbas, C.F.³

34
- 4143095871
- 10.1021/ar0300571 1:CAS:528:DC%2BD2cXjvVCks7c%3D
- B List 2004 Acc Chem Res 37 548 10.1021/ar0300571 1:CAS:528: DC%2BD2cXjvVCks7c%3D
- (2004) Acc Chem Res , vol.37 , pp. 548
- List, B.¹

35
- 38349100690
- 10.1021/cr0684016 1:CAS:528:DC%2BD2sXhsVSqsLrP
- S Mukherjee JW Yang S Hoffmann B List 2007 Chem Rev 107 5471 10.1021/cr0684016 1:CAS:528:DC%2BD2sXhsVSqsLrP
- (2007) Chem Rev , vol.107 , pp. 5471
- Mukherjee, S.¹ Yang, J.W.² Hoffmann, S.³ List, B.⁴

36
- 0003492804
- SSSR
- Golubev AS, Galakhov MV, Kolomiets AF, Fokin AV (1989) Izv Akad Nauk, SSSR, 2127
- (1989) Izv Akad Nauk , pp. 2127
- Golubev, A.S.¹ Galakhov, M.V.² Kolomiets, A.F.³ Fokin, A.V.⁴

37
- 7644241670
- Palecek J, Paleta O (2004) Synthesis 521
- (2004) Synthesis , pp. 521
- Palecek, J.¹ Paleta, O.²

38
- 33745259488
- Proline-catalyzed direct asymmetric aldol reaction of trifluoroacetaldehyde ethyl hemiacetal with ketones
- DOI 10.1016/j.tetlet.2006.05.165, PII S0040403906011087
- K Funabiki H Yamamoto H Nagaya M Matsui 2006 Tetrahedron Lett 47 5507 10.1016/j.tetlet.2006.05.165 1:CAS:528:DC%2BD28XmsVOqu7o%3D (Pubitemid 43929017)
- (2006) Tetrahedron Letters , vol.47 , Issue.31 , pp. 5507-5510
- Funabiki, K.¹ Yamamoto, H.² Nagaya, H.³ Matsui, M.⁴

39
- 33646508100
- 10.1021/jo0602017 1:CAS:528:DC%2BD28XjtFKhtr8%3D
- JT Suri S Mitsumori K Albertshofer F Tanaka CF Barbas 2006 J Org Chem 71 3822 10.1021/jo0602017 1:CAS:528:DC%2BD28XjtFKhtr8%3D
- (2006) J Org Chem , vol.71 , pp. 3822
- Suri, J.T.¹ Mitsumori, S.² Albertshofer, K.³ Tanaka, F.⁴ Barbas, C.F.⁵

40
- 0035813242
- A tentative rationalization of microwave effects in organic synthesis according to the reaction medium, and mechanistic considerations
- DOI 10.1016/S0040-4020(01)00905-X, PII S004040200100905X
- L Perreux A Loupy 2001 Tetrahedron 57 9199 10.1016/S0040-4020(01)00905-X 1:CAS:528:DC%2BD3MXnvFWlsrk%3D (Pubitemid 33019218)
- (2001) Tetrahedron , vol.57 , Issue.45 , pp. 9199-9223
- Perreux, L.¹ Loupy, A.²

41
- 14644427257
- Microwaves in organic synthesis. Thermal and non-thermal microwave effects
- DOI 10.1039/b411438h
- A De La Hoz A Diaz-Ortiz A Moreno 2005 Chem Soc Rev 34 164 10.1039/b411438h (Pubitemid 40311449)
- (2005) Chemical Society Reviews , vol.34 , Issue.2 , pp. 164-178
- De La Hoz, A.¹ Diaz-Ortiz, A.² Moreno, A.³

42
- 84924213784
- 10.1071/CH9951665 1:CAS:528:DyaK2MXovFOrs7k%3D
- CR Strauss RW Trainor 1995 Aust J Chem 48 1665 10.1071/CH9951665 1:CAS:528:DyaK2MXovFOrs7k%3D
- (1995) Aust J Chem , vol.48 , pp. 1665
- Strauss, C.R.¹ Trainor, R.W.²

43
- 70349219799
- World Patent, WO 04,002
- Hayes BL, Collins MJ Jr (2004) World Patent, WO 04,002,617
- (2004) , pp. 617
- Hayes, B.L.¹ Collins Jr, M.J.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.