메뉴 건너뛰기




Volumn 15, Issue 29, 2009, Pages 7039-7043

Highly enantioselective sulfenylation of β-ketoesters: H-bond acceptor catalysis

Author keywords

Asymmetric catalysis; Diarylprolinol organocatalysis; Quaternary stereocenter; Sulfenylation

Indexed keywords

AROMATIC RINGS; ASYMMETRIC CATALYSIS; BOND ACCEPTORS; DIARYLPROLINOL ORGANOCATALYSIS; ELECTRON-DONATING GROUP; ENANTIOSELECTIVE; HIGHER YIELD; KETO ESTER; MODEL SUBSTRATES; ORGANOCATALYTIC TRANSFORMATION; QUATERNARY STEREOCENTER; REACTION CONDITIONS; SIGNIFICANT FACTORS; STERICALLY DEMANDING; SULFENYLATION; TRIMETHYLSILYL ETHERS;

EID: 67650614934     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901099     Document Type: Article
Times cited : (71)

References (100)
  • 2
    • 67650604336 scopus 로고    scopus 로고
    • P. 1. Dalko, L. Moisan. Angew. Chem. 2004, 116, 5248-5286;
    • b) P. 1. Dalko, L. Moisan. Angew. Chem. 2004, 116, 5248-5286;
  • 3
    • 6044269452 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 5138-5175:
    • (2004) Angew. Chem. Int. Ed , vol.43 , pp. 5138-5175
  • 4
    • 4143094833 scopus 로고    scopus 로고
    • special Issue: Asymmetric Organocatalysis: Acc. Chem. Res. 2004, 37, 487-631;
    • c) special Issue: "Asymmetric Organocatalysis": Acc. Chem. Res. 2004, 37, 487-631;
  • 5
    • 67650642241 scopus 로고    scopus 로고
    • special Issue: Organocatalysis: Chem. Rev. 2007, 107, 5413-5883:
    • d) special Issue: "Organocatalysis": Chem. Rev. 2007, 107, 5413-5883:
  • 6
    • 67650609822 scopus 로고    scopus 로고
    • A. Dondoni, A. Massi, Angew. Chem. 2008, 120, 4716-4739: Angew. Chem. Int. Ed. 2008, 47, 4638-4660.
    • e) A. Dondoni, A. Massi, Angew. Chem. 2008, 120, 4716-4739: Angew. Chem. Int. Ed. 2008, 47, 4638-4660.
  • 13
    • 48749133072 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008. 47, 4719-4721;
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 4719-4721
  • 15
    • 48849106597 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 4722-4724:
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 4722-4724
  • 16
    • 40149110106 scopus 로고    scopus 로고
    • H. Kim, D. W. C. MacMillan, J. Am. Chem. Soc. 2008, 130, 398-399:
    • c) H. Kim, D. W. C. MacMillan, J. Am. Chem. Soc. 2008, 130, 398-399:
  • 18
    • 37349042884 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007. 46. 9202-9205.
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 9202-9205
  • 19
    • 0842343649 scopus 로고    scopus 로고
    • For C, O bond, see: a
    • For C - O bond, see: a) G. Zhong, Angew. Chem. 2003, 115, 4379-4382;
    • (2003) Angew. Chem , vol.115 , pp. 4379-4382
    • Zhong, G.1
  • 20
    • 0141522552 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 4247-4250;
    • (2003) Angew. Chem. Int. Ed , vol.42 , pp. 4247-4250
  • 22
    • 57749100152 scopus 로고    scopus 로고
    • -,Angew. Chem. Int. Ed. 2008, 47, 10187-10191.
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 10187-10191
  • 24
    • 33846551705 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 778-781:
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 778-781
  • 28
    • 34250157969 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 1983-1987.
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 1983-1987
  • 32
    • 53549103052 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 5796-5798.
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 5796-5798
  • 34
    • 13444267885 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 794-797;
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 794-797
  • 36
    • 54249164455 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 8468-8472.
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 8468-8472
  • 38
    • 34250707214 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 4504-4506:
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 4504-4506
  • 40
    • 67650609820 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46 507-4510.
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 507-4510
  • 42
    • 34548764427 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 6882-6885.
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 6882-6885
  • 43
    • 38349100690 scopus 로고    scopus 로고
    • For review, see: S. Mukherjee. J. Yang, S. Hoffmann, B. List. Chem. Rev. 2007, 107, 5471-5569.
    • For review, see: S. Mukherjee. J. Yang, S. Hoffmann, B. List. Chem. Rev. 2007, 107, 5471-5569.
  • 47
    • 0142131252 scopus 로고    scopus 로고
    • For catalysis by metal complexes, see, for example: a
    • For catalysis by metal complexes, see, for example: a) M. Marigo, K. Juhl, K. A. Jørgensen. Angew. Chem. 2003, 115, 1405-1407;
    • (2003) Angew. Chem , vol.115 , pp. 1405-1407
    • Marigo, M.1    Juhl, K.2    Jørgensen, K.A.3
  • 48
    • 0037471191 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 1367-1369:
    • (2003) Angew. Chem. Int. Ed , vol.42 , pp. 1367-1369
  • 53
    • 33947225755 scopus 로고    scopus 로고
    • J. Comelles, À. Pericas, M. Moreno-Mañas, A. Vallribera, G. Drudis-Solé. A. Lledos, T. Parella, A. Roglans, S. García-Granda, L. Roces-Fernández, J. Org. Chem. 2007, 76 2077-2087.
    • f) J. Comelles, À. Pericas, M. Moreno-Mañas, A. Vallribera, G. Drudis-Solé. A. Lledos, T. Parella, A. Roglans, S. García-Granda, L. Roces-Fernández, J. Org. Chem. 2007, 76 2077-2087.
  • 54
    • 34247853260 scopus 로고    scopus 로고
    • For phase-transfer catalysts, see, for example: a L. Bernardi, J. López-Cantarero, B. Niess, K. A. Jørgensen, J. Am. Chem. Soc. 2007, 129, 5772-5778;
    • For phase-transfer catalysts, see, for example: a) L. Bernardi, J. López-Cantarero, B. Niess, K. A. Jørgensen, J. Am. Chem. Soc. 2007, 129, 5772-5778;
  • 57
    • 0041363231 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 3796-3798;
    • (2003) Angew. Chem. Int. Ed , vol.42 , pp. 3796-3798
  • 62
    • 33749827801 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 6551-6554:
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 6551-6554
  • 64
    • 18844451481 scopus 로고    scopus 로고
    • For catalysis by cinchona-alkaloids and their derivatives, see, for example: a
    • For catalysis by cinchona-alkaloids and their derivatives, see, for example: a) H. Li. Y. Wang. L. Tang, F. Wu. X. Liu, C. Guo, B. M. Foxman, L. Deng, Angew. Chem. 2005, 117, 107-110:
    • (2005) Angew. Chem , vol.117 , pp. 107-110
    • Wang, H.L.Y.1    Tang, L.2    Wu, F.3    Liu, X.4    Guo, C.5    Foxman, B.M.6    Deng, L.7
  • 65
    • 33745370454 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 105-108;
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 105-108
  • 66
    • 67650632755 scopus 로고    scopus 로고
    • G. Bartoli, M. Bosco. A. Carlone. M. Localelli, P. Melchiorre, L. Sambri. Angew. Chem. 2005, 117, 6375-6378; Angew. Chem. Int. Ed. 2005, 44, 6219-6222;
    • b) G. Bartoli, M. Bosco. A. Carlone. M. Localelli, P. Melchiorre, L. Sambri. Angew. Chem. 2005, 117, 6375-6378; Angew. Chem. Int. Ed. 2005, 44, 6219-6222;
  • 69
    • 34547184381 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 5515-5519;
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 5515-5519
  • 73
    • 67650638986 scopus 로고    scopus 로고
    • Y. Yamaoka, H. Miyabe. Y. Yasui. Y. Takemoto, Synthesis 2007, 2571-2575; and one example of chiral guanidine: M. Terada, M. Nakano, H. Ube, J. Am. Chem. Soc. 2006, 128, 16044-16045.
    • b)Y. Yamaoka, H. Miyabe. Y. Yasui. Y. Takemoto, Synthesis 2007, 2571-2575; and one example of chiral guanidine: M. Terada, M. Nakano, H. Ube, J. Am. Chem. Soc. 2006, 128, 16044-16045.
  • 74
    • 6044262462 scopus 로고    scopus 로고
    • For an example of an imidazolidine catalyst as a base in a domino process, see: a
    • For an example of an imidazolidine catalyst as a base in a domino process, see: a) N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. 2004, 116, 1292-1291;
    • (2004) Angew. Chem , vol.116 , pp. 1292-1291
    • Halland, N.1    Aburel, P.S.2    Jørgensen, K.A.3
  • 75
    • 2342614099 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 1272-1277;
    • (2004) Angew. Chem. Int. Ed , vol.43 , pp. 1272-1277
  • 76
    • 33645775790 scopus 로고    scopus 로고
    • other limited examples, see: b A. Latlanzi. Tetrahedron: Asymmetry 2006, 17, 837-841:
    • other limited examples, see: b) A. Latlanzi. Tetrahedron: Asymmetry 2006, 17, 837-841:
  • 80
    • 58249120495 scopus 로고    scopus 로고
    • for an enol mechanism in a primary amine-thiourea catalyzed transformation, see: f
    • for an enol mechanism in a primary amine-thiourea catalyzed transformation, see: f) D. A. Yalalov, S. B. Tsogoeva. T. E. Shubina, I. M. Martynova, T. Clark. Angew. Chem. 2008, 120, 6726-6730;
    • (2008) Angew. Chem , vol.120 , pp. 6726-6730
    • Yalalov, D.A.1    Tsogoeva, S.B.2    Shubina, T.E.3    Martynova, I.M.4    Clark, T.5
  • 81
    • 53249084431 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 6624-6628.
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 6624-6628
  • 92
    • 67650578570 scopus 로고    scopus 로고
    • In fact, we discovered that there is a significant background reaction without any catalyst when 2h was tested as the substrate. This could partly account for its poor enantioselectivity displayed under identical reaction conditions
    • In fact, we discovered that there is a significant background reaction without any catalyst when 2h was tested as the substrate. This could partly account for its poor enantioselectivity displayed under identical reaction conditions.
  • 94
    • 33947576867 scopus 로고    scopus 로고
    • However, this synthetic method may be not applied to diaryl prolinols due to the steric effects
    • b) R. K. Vohra, J.-L. Renaud, C. Bruneau, Synthesis 2007, 731 -738. However, this synthetic method may be not applied to diaryl prolinols due to the steric effects.
    • (2007) Synthesis , pp. 731-738
    • Vohra, R.K.1    Renaud, J.-L.2    Bruneau, C.3
  • 95
    • 67650587277 scopus 로고    scopus 로고
    • Similar models have been reported for tertiary amine catalysts, for examples, see
    • Similar models have been reported for tertiary amine catalysts, for examples, see:
  • 98
    • 67650602052 scopus 로고    scopus 로고
    • See the Supporting Information for details
    • See the Supporting Information for details.
  • 99
    • 67650609819 scopus 로고    scopus 로고
    • 3 before use.
    • 3 before use.
  • 100
    • 67650617673 scopus 로고    scopus 로고
    • An amount of the keto form of 2e was also observed in the NMR spectra. However, the stable intramolecular H-bond signal completely disappeared on increasing the catalyst loading to 20mol, In fact, the sharp 1H NMR resonance is visible even in unpurified CDCl3, in which the equilibrium between the enol and the keto forms exists
    • 3, in which the equilibrium between the enol and the keto forms exists.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.