SCOPUS 정보 검색 플랫폼

Angewandte Chemie - International Edition

Volumn 50, Issue 10, 2011, Pages 2249-2252

Catalytic enantioselective protonation of α-oxygenated ester enolates prepared through phospha-brook rearrangement

(2) Hayashi, Masashi a Nakamura, Shuichi a

a NAGOYA INSTITUTE OF TECHNOLOGY (Japan)

Author keywords

Enantioselectivity; Enolates; Organocatalysis; Phospha Brook rearrangement; Protonation

Indexed keywords

BROOK REARRANGEMENT; CATALYST LOADINGS; CHEMICAL EQUATIONS; CINCHONA ALKALOID; ENANTIOSELECTIVE; ENANTIOSELECTIVE REACTIONS; ENOLATES; HIGH ENANTIOSELECTIVITY; KETO ESTER; ORGANOCATALYSIS; ORGANOCATALYTIC; PHOSPHONATES;

CATALYSIS; ESTERIFICATION; ESTERS; PROTONATION; RATE CONSTANTS; REACTION KINETICS; SODIUM;

ENANTIOSELECTIVITY;

EID: 79952047534 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201007568 Document Type: Article

Times cited : (119)

References (33)

1
- 0000530876
- For reviews on enantioselective protonation, see: a
- For reviews on enantioselective protonation, see: a) C. Fehr, Angew. Chem. 1996, 108, 2726-2748;
- (1996) Angew. Chem. , vol.108 , pp. 2726-2748
- Fehr, C.¹

2
- 33751146774
- Angew. Chem. Int. Ed. Engl. 1996, 35, 2566-2587;
- (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 2566-2587

3
- 0002284321
- b) A. Yanagisawa, K. Ishihara, H. Yamamoto, Synlett 1997, 411-420;
- (1997) Synlett , pp. 411-420
- Yanagisawa, A.¹ Ishihara, K.² Yamamoto, H.³

4
- 0035808857
- c) J. Eames, N. Weerasooriya, Tetrahedron: Asymmetry 2001, 12, 1-24;
- (2001) Tetrahedron: Asymmetry , vol.12 , pp. 1-24
- Eames, J.¹ Weerasooriya, N.²

5
- 9644291545
- d) L. Duhamel, P. Duhamel, J.-C. Plaquevent, Tetrahedron: Asymmetry 2004, 15, 3653-3691;
- (2004) Tetrahedron: Asymmetry , vol.15 , pp. 3653-3691
- Duhamel, L.¹ Duhamel, P.² Plaquevent, J.-C.³

6
- 69249201073
- e) J. T. Mohr, A. Y. Hong, B. M. Stoltz, Nat. Chem. 2009, 1, 359-369.
- (2009) Nat. Chem. , vol.1 , pp. 359-369
- Mohr, J.T.¹ Hong, A.Y.² Stoltz, B.M.³

7
- 0038682505
- and references therein
- K. Miyashita, M. Ikejiri, H. Kawasaki, S. Maemura, T. Imanishi, J. Am. Chem. Soc. 2003, 125, 8238-8243, and references therein.
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 8238-8243
- Miyashita, K.¹ Ikejiri, M.² Kawasaki, H.³ Maemura, S.⁴ Imanishi, T.⁵

8
- 66149136152
- W.-H. Jung, S. Guyenne, C. Riesco-Fagundo, J. Mancuso, S. Nakamura, D. P. Curran, Angew. Chem. 2008, 120, 1146-1149;
- (2008) Angew. Chem. , vol.120 , pp. 1146-1149
- Jung, W.-H.¹ Guyenne, S.² Riesco-Fagundo, C.³ Mancuso, J.⁴ Nakamura, S.⁵ Curran, D.P.⁶

9
- 38849143925
- and references therein
- Angew. Chem. Int. Ed. 2008, 47, 1130-1133, and references therein.
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 1130-1133

10
- 77955048478
- and references therein
- N. Oku, K. Takada, R. W. Fuller, J. A. Wilson, M. L. Peach, L. K. Pannell, J. B. McMahon, K. R. Gustafson, J. Am. Chem. Soc. 2010, 132, 10278-10285, and references therein.
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 10278-10285
- Oku, N.¹ Takada, K.² Fuller, R.W.³ Wilson, J.A.⁴ Peach, M.L.⁵ Pannell, L.K.⁶ McMahon, J.B.⁷ Gustafson, K.R.⁸

11
- 0035845686
- a) M. Graupner, R. H. White, Biochemistry 2001, 40, 10859-10872;
- (2001) Biochemistry , vol.40 , pp. 10859-10872
- Graupner, M.¹ White, R.H.²

12
- 79952060785
- b) A. Sakakura, M. Katsukawa, K. Ishihara, Angew. Chem. 2007, 119, 1445-1448;
- (2007) Angew. Chem. , vol.119 , pp. 1445-1448
- Sakakura, A.¹ Katsukawa, M.² Ishihara, K.³

13
- 34247890173
- Angew. Chem. Int. Ed. 2007, 46, 1423-1426;
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 1423-1426

14
- 67650471372
- c) T. Murai, T. Takenaka, S. Inaji, Y. Tonomura, Chem. Lett. 2008, 37, 1198-1199;
- (2008) Chem. Lett. , vol.37 , pp. 1198-1199
- Murai, T.¹ Takenaka, T.² Inaji, S.³ Tonomura, Y.⁴

15
- 77949357065
- and references therein
- d) H. Ohmiya, U. Yokobori, Y. Makida, M. Sawamura, J. Am. Chem. Soc. 2010, 132, 2895-2897, and references therein.
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 2895-2897
- Ohmiya, H.¹ Yokobori, U.² Makida, Y.³ Sawamura, M.⁴

16
- 45449125785
- For racemic phospha-Brook rearrangement of ketones with phosphites, see: a
- For racemic phospha-Brook rearrangement of ketones with phosphites, see: a) M. Kuroboshi, T. Ishihara, T. Ando, J. Fluorine Chem. 1988, 39, 293-298;
- (1988) J. Fluorine Chem. , vol.39 , pp. 293-298
- Kuroboshi, M.¹ Ishihara, T.² Ando, T.³

17
- 25444510404
- and references therein
- b) L. El Kaïm, L. Gaultier, L. Grimaud, A. D. Santos, Synlett 2005, 2335-2336, and references therein.
- (2005) Synlett , pp. 2335-2336
- El Kaïm, L.¹ Gaultier, L.² Grimaud, L.³ Santos, A.D.⁴

18
- 58449111212
- For enantioselective hydrophosphonylation to ketones, see: a
- For enantioselective hydrophosphonylation to ketones, see: a) F. Wang, X. Liu, X. Cui, Y. Xiong, X. Zhou, X. Feng, Chem. Eur. J. 2009, 15, 589-592;
- (2009) Chem. Eur. J. , vol.15 , pp. 589-592
- Wang, F.¹ Liu, X.² Cui, X.³ Xiong, Y.⁴ Zhou, X.⁵ Feng, X.⁶

19
- 70549103416
- b) X. Zhou, Y. Liu, L. Chang, J. Zhao, D. Shang, X. Liu, L. Lin, X. Feng, Adv. Synth. Catal. 2009, 351, 2567-2572;
- (2009) Adv. Synth. Catal. , vol.351 , pp. 2567-2572
- Zhou, X.¹ Liu, Y.² Chang, L.³ Zhao, J.⁴ Shang, D.⁵ Liu, X.⁶ Lin, L.⁷ Feng, X.⁸

20
- 79551537564
- c) D. Uraguchi, T. Ito, S. Nakamura, T. Ooi, Chem. Sci. 2010, 1, 488-490;
- (2010) Chem. Sci. , vol.1 , pp. 488-490
- Uraguchi, D.¹ Ito, T.² Nakamura, S.³ Ooi, T.⁴

21
- 77957174098
- d) X. Zhou, Q. Zhang, Y. Hui, W. Chen, J. Jiang, L. Lin, X. Liu, X. Feng, Org. Lett. 2010, 12, 4296-4299.
- (2010) Org. Lett. , vol.12 , pp. 4296-4299
- Zhou, X.¹ Zhang, Q.² Hui, Y.³ Chen, W.⁴ Jiang, J.⁵ Lin, L.⁶ Liu, X.⁷ Feng, X.⁸

22
- 0034677676
- For review on enantioselective hydrophosphonylation of aldehydes, see: a
- For review on enantioselective hydrophosphonylation of aldehydes, see: a) H. Gröger, B. Hammer, Chem. Eur. J. 2000, 6, 943-948;
- (2000) Chem. Eur. J. , vol.6 , pp. 943-948
- Gröger, H.¹ Hammer, B.²

23
- 49249117085
- and references therein
- b) P. Merino, E. Marqués-López, R. P. Herrera, Adv. Synth. Catal. 2008, 350, 1195-1208, and references therein.
- (2008) Adv. Synth. Catal. , vol.350 , pp. 1195-1208
- Merino, P.¹ Marqués-López, E.² Herrera, R.P.³

24
- 73249115987
- S. Nakamura, M. Hayashi, Y. Hiramatsu, N. Shibata, Y. Funahashi, T. Toru, J. Am. Chem. Soc. 2009, 131, 18240-18241.
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 18240-18241
- Nakamura, S.¹ Hayashi, M.² Hiramatsu, Y.³ Shibata, N.⁴ Funahashi, Y.⁵ Toru, T.⁶

25
- 49249103067
- We also reported the enantioselective reaction of N-sulfonylimines with phosphite using cinchona alkaloids catalysts, see
- We also reported the enantioselective reaction of N-sulfonylimines with phosphite using cinchona alkaloids catalysts, see: S. Nakamura, H. Nakashima, A. Yamamura, N. Shibata, T. Toru, Adv. Synth. Catal. 2008, 350, 1209-1212.
- (2008) Adv. Synth. Catal. , vol.350 , pp. 1209-1212
- Nakamura, S.¹ Nakashima, H.² Yamamura, A.³ Shibata, N.⁴ Toru, T.⁵

26
- 0034045413
- For catalytic enantioselective protonation using cinchona alkaloid derivatives, see: a
- For catalytic enantioselective protonation using cinchona alkaloid derivatives, see: a) H. Brunner, P. Schmidt, Eur. J. Org. Chem. 2000, 2119-2133;
- (2000) Eur. J. Org. Chem. , pp. 2119-2133
- Brunner, H.¹ Schmidt, P.²

27
- 33646812942
- b) T. Seitz, J. Baudoux, H. Bekolo, D. Cahard, J.-C. Plaquevent, M.-C. Lasne, J. Rouden, Tetrahedron 2006, 62, 6155-6165;
- (2006) Tetrahedron , vol.62 , pp. 6155-6165
- Seitz, T.¹ Baudoux, J.² Bekolo, H.³ Cahard, D.⁴ Plaquevent, J.-C.⁵ Lasne, M.-C.⁶ Rouden, J.⁷

28
- 53549095018
- c) T. Poisson, V. Dalla, F. Marsais, G. Dupas, S. Oudeyer, V. Levacher, Angew. Chem. 2007, 119, 7220-7223;
- (2007) Angew. Chem. , vol.119 , pp. 7220-7223
- Poisson, T.¹ Dalla, V.² Marsais, F.³ Dupas, G.⁴ Oudeyer, S.⁵ Levacher, V.⁶

29
- 34848866929
- Angew. Chem. Int. Ed. 2007, 46, 7090-7093;
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 7090-7093

30
- 47749084742
- For catalytic enantioselective protonation using organocatalysts, see: d
- For catalytic enantioselective protonation using organocatalysts, see: d) C. H. Cheon, H. Yamamoto, J. Am. Chem. Soc. 2008, 130, 9246-9247;
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 9246-9247
- Cheon, C.H.¹ Yamamoto, H.²

31
- 77956241458
- e) D. Uraguchi, N. Kinoshita, T. Ooi, J. Am. Chem. Soc. 2010, 132, 12240-12242;
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 12240-12242
- Uraguchi, D.¹ Kinoshita, N.² Ooi, T.³

32
- 57549100052
- f) D. Leow, S. Lin, S. K. Chittimalla, X. Fu, C.-H. Tan, Angew. Chem. 2008, 120, 5723;
- (2008) Angew. Chem. , vol.120 , pp. 5723
- Leow, D.¹ Lin, S.² Chittimalla, S.K.³ Fu, X.⁴ Tan, C.-H.⁵

33
- 49649104027
- Angew. Chem. Int. Ed. 2008, 47, 5641.
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 5641

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.