SCOPUS 정보 검색 플랫폼

Volumn 8, Issue , 2012, Pages 1279-1283

Asymmetric organocatalytic decarboxylative Mannich reaction using β-keto acids: A new protocol for the synthesis of chiral â-amino ketones

(3) Jiang, Chunhui a Zhong, Fangrui a Lu, Yixin a

a NATIONAL UNIVERSITY OF SINGAPORE (Singapore)

Author keywords

keto acid; Decarboxylative addition; Mannich reaction; Organocatalysis

Indexed keywords

EID: 84865211796 PISSN: None EISSN: 18605397 Source Type: Journal
DOI: 10.3762/bjoc.8.144 Document Type: Article

Times cited : (45)

References (48)

1
- 0027383857
- 1,3-Amino alcohols from 4-amino-1-aza dienes. Diastereo- and enantioselective approach to the four diastereoisomers of the N-terminal amino acid component of nikkomycins B and B(x)
- DOI 10.1021/jo00074a024
- Barluenga, J.; Viado, A. L; Aguilar, E.; Fustero, S.; Olano, B. J. Org. Chem. 1993, 58, 5972-5975. doi:10.1021/jo00074a024 (Pubitemid 23363009)
- (1993) Journal of Organic Chemistry , vol.58 , Issue.22 , pp. 5972-5975
- Barluenga, J.¹ Viado, A.L.² Aguilar, E.³ Fustero, S.⁴ Olano, B.⁵

2
- 4444243696
- Diastereo- and enantioselective synthesis of differently N,O-protected 1,3-amino alcohols with three neighbouring stereogenic centers
- DOI 10.1055/s-2004-829142
- Enders, D.; Moser, M.; Geibel, G.; Laufer, M. C. Synthesis 2004, 2040-2046. doi:10.1055/s-2004-829142 (Pubitemid 39194309)
- (2004) Synthesis , Issue.12 , pp. 2040-2046
- Enders, D.¹ Moser, M.² Geibel, G.³ Laufer, M.C.⁴

3
- 0031562069
- Cobalt catalyzed multiple component condensation route to acetamido carbonyl compound libraries
- DOI 10.1016/S0040-4039(96)02474-4, PII S0040403996024744
- Mukhopadhyay, M.; Bhatia, B.; Iqbal, J. Tetrahedron Lett. 1997, 38, 1083-1086. doi:10.1016/S0040-4039(96)02474-4 (Pubitemid 27073554)
- (1997) Tetrahedron Letters , vol.38 , Issue.6 , pp. 1083-1086
- Mukhopadhyay, M.¹ Bhatia, B.² Iqbal, J.³

4
- 0032482080
- doi:10.1002/(SICI)1521-3773(19980504)37:8<1044:AID-ANIE1044>3. 0.CO;2-E
- Arend, M.; Westerman, B.; Risch, N. Angew. Chem., Int. Ed. 1998, 37, 1044-1070. doi:10.1002/(SICI)1521-3773(19980504)37:8<1044:AID-ANIE1044>3. 0.CO;2-E
- (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 1044-1070
- Arend, M.¹ Westerman, B.² Risch, N.³

5
- 0142106430
- Synthesis of a transition state analogue inhibitor of purine nucleoside phosphorylase via the Mannich reaction
- DOI 10.1021/ol035293q
- Evans, G. B.; Furneaux, R. H.; Tyler, P. C; Schramm, V. L. Org. Lett. 2003, 5, 3639-3640. doi:10.1021/ol035293q (Pubitemid 37289543)
- (2003) Organic Letters , vol.5 , Issue.20 , pp. 3639-3640
- Evans, G.B.¹ Furneaux, R.H.² Tyler, P.C.³ Schramm, V.L.⁴

6
- 10344251551
- A three-component Mannich-type reaction for selective tyrosine bioconjugation
- DOI 10.1021/ja0439017
- Joshi, N. S.; Whitaker, L. R.; Francis, M. B. J. Am. Chem. Soc. 2004, 126, 15942-15943. doi:10.1021/ja0439017 (Pubitemid 39627587)
- (2004) Journal of the American Chemical Society , vol.126 , Issue.49 , pp. 15942-15943
- Joshi, N.S.¹ Whitaker, L.R.² Francis, M.B.³

7
- 0000862669
- doi:10.1021/cr980414z
- Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069-1094. doi:10.1021/cr980414z
- (1999) Chem. Rev. , vol.99 , pp. 1069-1094
- Kobayashi, S.¹ Ishitani, H.²

8
- 0030788354
- Catalytic enantioseleetive Mannich-type reactions using a novel chiral zirconium catalyst [3]
- DOI 10.1021/ja970498d
- Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153-7154. doi:10.1021/ja970498d (Pubitemid 27357307)
- (1997) Journal of the American Chemical Society , vol.119 , Issue.30 , pp. 7153-7154
- Ishitani, H.¹ Ueno, M.² Kobayashi, S.³

9
- 0032554058
- Catalytic asymmetric synthesis of both syn- and anti-amino alcohols
- DOI 10.1021/ja973527t
- Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431-432. doi:10.1021/ja973527t (Pubitemid 28062532)
- (1998) Journal of the American Chemical Society , vol.120 , Issue.2 , pp. 431-432
- Kobayashi, S.¹ Ishitani, H.² Ueno, M.³

10
- 0032542749
- Enantioselective addition of enol silyl ethers to imines catalyzed by palladium complexes: A novel way to optically active acylalanine derivatives
- DOI 10.1021/ja973962n
- Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475. doi:10.1021/ja973962n (Pubitemid 28149796)
- (1998) Journal of the American Chemical Society , vol.120 , Issue.10 , pp. 2474-2475
- Hagiwara, E.¹ Fuji, A.² Sodeoka, M.³

11
- 0034734313
- doi:10.1021/ja001642p
- Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 8180-8186. doi:10.1021/ja001642p
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 8180-8186
- Ishitani, H.¹ Ueno, M.² Kobayashi, S.³

12
- 0035902842
- doi:10.1002/1521-3773(20010817)40:16<2995:AID-ANIE2995>3.0.CO;2-M
- Juhl, K.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2995-2997. doi:10.1002/1521-3773(20010817)40:16<2995:AID- ANIE2995>3.0.CO;2-M
- (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 2995-2997
- Juhl, K.¹ Gathergood, N.² Jørgensen, K.A.³

13
- 0037244819
- doi:10.1021/ar020137p
- Taggi, A. E.; Hafez, A. E.; Lectka, T. Acc. Chem. Res. 2003, 36, 10-19. doi:10.1021/ar020137p
- (2003) Acc. Chem. Res. , vol.36 , pp. 10-19
- Taggi, A.E.¹ Hafez, A.E.² Lectka, T.³

14
- 4143114533
- doi:10.1021/ar0300468
- Notz, W.; Tanaka, F.; Barbas, C. F., III. Acc. Chem. Res. 2004, 37, 580-591. doi:10.1021/ar0300468
- (2004) Acc. Chem. Res. , vol.37 , pp. 580-591
- Notz, W.¹ Tanaka, F.² Barbas Iii, C.F.³

15
- 38349100690
- doi:10.1021/cr0684016
- Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471-5569. doi:10.1021/cr0684016
- (2007) Chem. Rev. , vol.107 , pp. 5471-5569
- Mukherjee, S.¹ Yang, J.W.² Hoffmann, S.³ List, B.⁴

16
- 53549121402
- doi:10.1002/anie.200705523
- Melchiorre, P.; Marigo, M.; Carlone, A.; Bartoli, G. Angew. Chem., Int. Ed. 2008, 47, 6138-6171. doi:10.1002/anie.200705523
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 6138-6171
- Melchiorre, P.¹ Marigo, M.² Carlone, A.³ Bartoli, G.⁴

17
- 55849135242
- doi:10.1039/B809301F
- Kano, T.; Maruoka, K. Chem. Commun. 2008, 5465-5473. doi:10.1039/B809301F
- (2008) Chem. Commun. , pp. 5465-5473
- Kano, T.¹ Maruoka, K.²

18
- 38349189109
- doi:10.1021/cr068374j
- Akiyama, T. Chem. Rev. 2007, 107, 5744-5758. doi:10.1021/cr068374j
- (2007) Chem. Rev. , vol.107 , pp. 5744-5758
- Akiyama, T.¹

19
- 38149118178
- doi:10.1039/b713885g
- Verkade, J. M. M.; van Hemert, L. J. C; Quaedflieg, P. J. L. M.; Rutjes, F. P. J. T. Chem. Soc. Rev. 2008, 37, 29-41. doi:10.1039/b713885g
- (2008) Chem. Soc. Rev. , vol.37 , pp. 29-41
- Verkade, J.M.M.¹ Van Hemert, L.J.C.² Quaedflieg, P.J.L.M.³ Rutjes, F.P.J.T.⁴

20
- 34250760386
- Development of the first Brnsted acid assisted enantioselective Brnsted acid catalyzed direct Mannich reaction
- DOI 10.1055/s-2007-980369
- Rueping, M.; Sugiono, E.; Schoepke, F. R. Synlett 2007, 1441-1445. doi:10.1055/s-2007-980369 (Pubitemid 46957386)
- (2007) Synlett , Issue.9 , pp. 1441-1445
- Rueping, M.¹ Sugiono, E.² Schoepke, F.R.³

21
- 0037433513
- An exceptionally mild catalytic thioester aldol reaction inspired by polyketide biosynthesis
- DOI 10.1021/ja029452x
- Lalic, G.; Aloise, A. D.; Shair, M.D. J. Am. Chem. Soc. 2003, 125, 2852-2853. doi:10.1021/ja029452x (Pubitemid 36512491)
- (2003) Journal of the American Chemical Society , vol.125 , Issue.10 , pp. 2852-2853
- Lalic, G.¹ Aloise, A.D.² Shair, M.D.³

22
- 0842326656
- Cu(II)-catalyzed enantioselective aldol condensation between malonic acid hemithioesters and aldehydes
- DOI 10.1016/j.tetlet.2003.12.089
- Orlandi, S.; Benaglia, M.; Cozzi, F. Tetrahedron Lett. 2004, 45, 1747-1749. doi:10.1016/j.tetlet.2003.12.089 (Pubitemid 38169314)
- (2004) Tetrahedron Letters , vol.45 , Issue.8 , pp. 1747-1749
- Orlandi, S.¹ Benaglia, M.² Cozzi, F.³

23
- 19744363827
- Catalytic enantioselective thioester aldol reactions that are compatible with protic functional groups
- DOI 10.1021/ja051759j
- Magdziak, D.; Lalic, G.; Lee, H. M.; Fortner, K. C; Aloise, A. D.; Shair, M. D. J. Am. Chem. Soc. 2005, 127, 7284-7285. doi:10.1021/ja051759j (Pubitemid 40745994)
- (2005) Journal of the American Chemical Society , vol.127 , Issue.20 , pp. 7284-7285
- Magdziak, D.¹ Lalic, G.² Lee, H.M.³ Fortner, K.C.⁴ Aloise, A.D.⁵ Shair, M.D.⁶

24
- 33846842435
- Stereoelectronic effects dictate mechanistic dichotomy between Cu(II)-catalyzed and enzyme-catalyzed reactions of malonic acid half thioesters
- DOI 10.1021/ja0673682
- Fortner, K. C.; Shair, M. D. J. Am. Chem. Soc. 2007, 129, 1032-1033. doi:10.1021/ja0673682 (Pubitemid 46208563)
- (2007) Journal of the American Chemical Society , vol.129 , Issue.5 , pp. 1032-1033
- Fortner, K.C.¹ Shair, M.D.²

25
- 78349300216
- doi:10.1002/asia.201000540
- Furutachi, M.; Mouri, S.; Matsunaga, S.; Shibasaki, M. Chem. Asian J. 2010, 5, 2351-2354. doi:10.1002/asia.201000540
- (2010) Chem. Asian J. , vol.5 , pp. 2351-2354
- Furutachi, M.¹ Mouri, S.² Matsunaga, S.³ Shibasaki, M.⁴

26
- 0001315449
- doi:10.1007/BF00807023
- Brunner, H.; Müller, J.; Spitzer, J. Monatsh. Chem. 1996, 127, 845-858. doi:10.1007/BF00807023
- (1996) Monatsh. Chem. , vol.127 , pp. 845-858
- Brunner, H.¹ Müller, J.² Spitzer, J.³

27
- 0042836556
- Self-condensation of activated malonic acid half esters: A model for the decarboxylative Claisen condensation in polyketide biosynthesis
- DOI 10.1016/j.tetlet.2003.08.014
- Ryu, Y.; Scott, A. I. Tetrahedron Lett. 2003, 44, 7499-7502. doi:10.1016/j.tetlet.2003.08.014 (Pubitemid 37102986)
- (2003) Tetrahedron Letters , vol.44 , Issue.40 , pp. 7499-7502
- Ryu, Y.¹ Scott, A.I.²

28
- 27544497003
- Practical synthesis of (E)-,-unsaturated esters from aldehydes
- DOI 10.1002/adsc.200505196
- List, B.; Doehring, A.; Fonseca, M. T. H.; Wobser, K.; van Thienen, H.; Torres, R. R.; Galilea, P. Adv. Synth. Catal. 2005, 347, 1558-1560. doi:10.1002/adsc.200505196 (Pubitemid 41542798)
- (2005) Advanced Synthesis and Catalysis , vol.347 , Issue.11-13 , pp. 1558-1560
- List, B.¹ Doehring, A.² Fonseca, M.T.H.³ Wobser, K.⁴ Van Thienen, H.⁵ Torres, R.R.⁶ Galilea, P.L.⁷

29
- 56049094107
- doi:10.1002/ejoc.200800759
- Blanchet, J.; Baudoux, J.; Amere, M.; Lasne, M. C.; Rouden, J. Eur. J. Org. Chem. 2008, 5493-5506. doi:10.1002/ejoc.200800759
- (2008) Eur. J. Org. Chem. , pp. 5493-5506
- Blanchet, J.¹ Baudoux, J.² Amere, M.³ Lasne, M.C.⁴ Rouden, J.⁵

30
- 70349144936
- doi:10.1021/jo901022j
- Blaquiere, N.; Shore, D. G.; Rousseaux, S.; Fagnou, K. J. Org. Chem. 2009, 74, 6190-6198. doi:10.1021/jo901022j
- (2009) J. Org. Chem. , vol.74 , pp. 6190-6198
- Blaquiere, N.¹ Shore, D.G.² Rousseaux, S.³ Fagnou, K.⁴

31
- 34547186720
- doi:10.1002/adsc.200600536
- Ricci, A.; Pettersen, D.; Bernardi, L; Fini, F.; Fochi, M.; Herrera, R. P.; Sgarzani, V. Adv. Synth. Catal. 2007, 349, 1037-1040. doi:10.1002/adsc. 200600536
- (2007) Adv. Synth. Catal. , vol.349 , pp. 1037-1040
- Ricci, A.¹ Pettersen, D.² Bernardi, L.³ Fini, F.⁴ Fochi, M.⁵ Herrera, R.P.⁶ Sgarzani, V.⁷

32
- 34548771245
- Mimicry of polyketide synthases - Enantioselective 1,4-addition reactions of malonic acid half-thioesters to nitroolefins
- DOI 10.1002/anie.200702187
- Lubkoll, J.; Wennemers, H. Angew. Chem., Int. Ed. 2007, 46, 6841-6844. doi:10.1002/anie.200702187 (Pubitemid 47425800)
- (2007) Angewandte Chemie - International Edition , vol.46 , Issue.36 , pp. 6841-6844
- Lubkoll, J.¹ Wennemers, H.²

33
- 79960299444
- doi:10.1002/chem.201100687
- Pan, Y.; Kee, C. W.; Jiang, Z.; Ma, T.; Zhao, Y.; Yang, Y.; Xue, H.; Tan, C. H. Chem. Eur. J. 2011, 17, 8363-8370. doi:10.1002/chem.201100687
- (2011) Chem. Eur. J. , vol.17 , pp. 8363-8370
- Pan, Y.¹ Kee, C.W.² Jiang, Z.³ Ma, T.⁴ Zhao, Y.⁵ Yang, Y.⁶ Xue, H.⁷ Tan, C.H.⁸

34
- 82055163073
- doi:10.1002/adsc.201100458
- Bae, H. Y.; Some, S.; Lee, J. H.; Kim, J. Y.; Song, M. J.; Lee, S.; Zhang, Y. J.; Song, C. E. Adv. Synth. Catal. 2011, 353, 3196-3202. doi:10.1002/adsc.201100458
- (2011) Adv. Synth. Catal. , vol.353 , pp. 3196-3202
- Bae, H.Y.¹ Some, S.² Lee, J.H.³ Kim, J.Y.⁴ Song, M.J.⁵ Lee, S.⁶ Zhang, Y.J.⁷ Song, C.E.⁸

35
- 76349094086
- doi:10.1039/b915681j
- Baudoux, J.; Lefebvre, P.; Legay, R.; Lasne, M. C.; Rouden, J. Green Chem. 2010, 12, 252-259. doi:10.1039/b915681j
- (2010) Green Chem. , vol.12 , pp. 252-259
- Baudoux, J.¹ Lefebvre, P.² Legay, R.³ Lasne, M.C.⁴ Rouden, J.⁵

36
- 81555226801
- doi:10.1002/adsc.201100410
- Hara, N.; Nakamura, S.; Funahashi, Y.; Shibata, N. Adv. Synth. Catal. 2011, 353, 2976-2980. doi:10.1002/adsc.201100410
- (2011) Adv. Synth. Catal. , vol.353 , pp. 2976-2980
- Hara, N.¹ Nakamura, S.² Funahashi, Y.³ Shibata, N.⁴

37
- 84859576678
- doi:10.1039/c2cc30949a
- Zheng, Y.; Xiong, H. Y.; Nie, J.; Hua, M. Q.; Ma, J. A. Chem. Commun. 2012, 48, 4308-4310. doi:10.1039/c2cc30949a
- (2012) Chem. Commun. , vol.48 , pp. 4308-4310
- Zheng, Y.¹ Xiong, H.Y.² Nie, J.³ Hua, M.Q.⁴ Ma, J.A.⁵

38
- 84862557665
- doi:10.1021/ol301180z
- Yang, C. F.; Shen, C.; Wang, J. Y.; Tian, S. K. Org. Lett. 2012, 14, 3092-3095. doi:10.1021/ol301180z
- (2012) Org. Lett. , vol.14 , pp. 3092-3095
- Yang, C.F.¹ Shen, C.² Wang, J.Y.³ Tian, S.K.⁴

39
- 80051692462
- doi:10.1055/s-0030-1260607
- Pan, Y.; Tan, C. H. Synthesis 2011, 2044-2053. doi:10.1055/s-0030-1260607
- Synthesis , vol.2011 , pp. 2044-2053
- Pan, Y.¹ Tan, C.H.²

40
- 58949092249
- doi:10.1021/ol802486m
- Luo, J.; Xu, L. W.; Hay, R. A. S.; Lu, Y. Org. Lett. 2009, 11, 437-440. doi:10.1021/ol802486m
- (2009) Org. Lett. , vol.11 , pp. 437-440
- Luo, J.¹ Xu, L.W.² Hay, R.A.S.³ Lu, Y.⁴

41
- 33845220042
- Cupreines and cupreidines: An emerging class of bifunctional cinchona organocatalysts
- DOI 10.1002/anie.200602318
- Marcelli, T.; Maarseveen, J. H.; Huiemstra, H. Angew. Chem., Int. Ed. 2006, 45, 7496-7504. doi:10.1002/anie.200602318 (Pubitemid 44851670)
- (2006) Angewandte Chemie - International Edition , vol.45 , Issue.45 , pp. 7496-7504
- Marcelli, T.¹ Van Maarseveen, J.H.² Hiemstra, H.³

42
- 78650855864
- doi:10.1021/ol102597s
- Zhong, F.; Chen, G. Y.; Lu, Y. Org. Lett. 2011, 13, 82-85. doi:10.1021/ol102597s
- (2011) Org. Lett. , vol.13 , pp. 82-85
- Zhong, F.¹ Chen, G.Y.² Lu, Y.³

43
- 44949251617
- Primary amino acids: Privileged catalysts in enantioselective organocatalysis
- DOI 10.1039/b803116a
- Xu, L. W.; Lu, Y. Org. Biomol. Chem. 2008, 6, 2047-2053. doi:10.1039/b803116a (Pubitemid 351808226)
- (2008) Organic and Biomolecular Chemistry , vol.6 , Issue.12 , pp. 2047-2053
- Xu, L.-W.¹ Lu, Y.²

44
- 67549137639
- doi:10.1039/b821070e
- Xu, L. W.; Luo, J.; Lu, Y. Chem. Commun. 2009, 1807-1821. doi:10.1039/b821070e
- (2009) Chem. Commun. , pp. 1807-1821
- Xu, L.W.¹ Luo, J.² Lu, Y.³

45
- 84555190096
- doi:10.1002/chem.201102796
- Dou, X.; Han, X.; Lu, Y. Chem. Eur. J. 2012, 18, 85-89. doi:10.1002/chem.201102796
- (2012) Chem. Eur. J. , vol.18 , pp. 85-89
- Dou, X.¹ Han, X.² Lu, Y.³

46
- 70349995077
- doi:10.1002/anie.200903635
- Han, X.; Kwiatkowski, J.; Xue, F.; Huang, K. W.; Lu, Y. Angew. Chem., Int. Ed. 2009, 48, 7604-7607. doi:10.1002/anie.200903635
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 7604-7607
- Han, X.¹ Kwiatkowski, J.² Xue, F.³ Huang, K.W.⁴ Lu, Y.⁵

47
- 78249252089
- doi:10.1002/anie.201003837
- Zhu, Q.; Lu, Y. Angew. Chem., Int. Ed. 2010, 49, 7753-7756. doi:10.1002/anie.201003837
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 7753-7756
- Zhu, Q.¹ Lu, Y.²

48
- 33745850448
- doi:10.1002/ejoc.200600147
- Zhao, C. H.; Liu, L.; Wang, D.; Chen, Y. J. Eur. J. Org. Chem. 2006, 2977-2986. doi:10.1002/ejoc.200600147
- (2006) Eur. J. Org. Chem. , pp. 2977-2986
- Zhao, C.H.¹ Liu, L.² Wang, D.³ Chen, Y.J.⁴

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.