메뉴 건너뛰기




Volumn 17, Issue 23, 2011, Pages 6484-6491

Enantioselective intramolecular crossed rauhut-currier reactions through cooperative nucleophilic activation and hydrogen-bonding catalysis: Scope and mechanistic insight

Author keywords

asymmetric catalysis; cascade reactions; hydrogen bonds; Michael addition; Rauhut Currier reaction

Indexed keywords

ASYMMETRIC CATALYSIS; CASCADE REACTIONS; CHEMOSELECTIVE; COMPUTATIONAL INVESTIGATION; DIASTEREO-SELECTIVITY; ENANTIOSELECTIVE; EXPERIMENTAL PROCEDURE; HYDROGEN BONDINGS; MICHAEL ADDITIONS; NITROOLEFINS; NUCLEOPHILIC ACTIVATION; RAUHUT-CURRIER REACTION; SYNTHETIC APPLICATION;

EID: 79958217047     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201100479     Document Type: Article
Times cited : (79)

References (119)
  • 1
    • 79958220243 scopus 로고    scopus 로고
    • For a review, see
    • For a review, see
  • 3
    • 79958201463 scopus 로고
    • Ger. Offen. DE 2155113
    • A. B. Baylis, M. E. D. Hillman, Celanese Corp., Ger. Offen. DE 2155113, 1972
    • (1972)
    • Baylis, A.B.1    Hillman, M.E.D.2
  • 4
    • 0003744531 scopus 로고    scopus 로고
    • 77, 434174
    • Chem. Abstr. 1972, 77, 434174
    • Chem. Abstr. , pp. 1972
  • 6
    • 79958226866 scopus 로고
    • U.S. Patent 307499919630122
    • M. M. Rauhut, H. Currier, American Cyanamid Co., U.S. Patent 307499919630122, 1963
    • (1963)
    • Rauhut, M.M.1    Currier, H.2
  • 7
    • 5144227748 scopus 로고
    • Chem. Abstr. 1963, 58, 11 224a.
    • (1963) Chem. Abstr. , vol.58 , pp. 11224
  • 8
    • 48849102178 scopus 로고    scopus 로고
    • For a Lewis acid-catalyzed reaction, see
    • For a Lewis acid-catalyzed reaction, see:, T. E. Reynolds, M. S. Binkley, K. A. Scheidt, Org. Lett. 2008, 10, 2449-2452.
    • (2008) Org. Lett. , vol.10 , pp. 2449-2452
    • Reynolds, T.E.1    Binkley, M.S.2    Scheidt, K.A.3
  • 13
    • 79958201166 scopus 로고    scopus 로고
    • For representative examples, see
    • For representative examples, see
  • 15
    • 71949129054 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 9713-9716
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 9713-9716
  • 17
    • 60149088814 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 1279-1282
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 1279-1282
  • 19
    • 33746211437 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 3117-3119
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 3117-3119
  • 23
    • 79958217963 scopus 로고    scopus 로고
    • Although the RC reaction was first reported in 1963, there are few reports on the enantioselective variants to date; see
    • Although the RC reaction was first reported in 1963, there are few reports on the enantioselective variants to date; see
  • 26
    • 34247156603 scopus 로고    scopus 로고
    • during the preparation of this report, Wu and co-workers developed the first example of a bifunctional phosphinothiourea-catalyzed enantioselective intramolecular Rauhut-Currier reaction of bis-enones, see
    • F. Seidel, J. A. Gladysz, Synlett 2007, 0986-0988; during the preparation of this report, Wu and co-workers developed the first example of a bifunctional phosphinothiourea-catalyzed enantioselective intramolecular Rauhut-Currier reaction of bis-enones, see
    • (2007) Synlett , pp. 0986-0988
    • Seidel, F.1    Gladysz, J.A.2
  • 29
    • 53549133989 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 4177-4179.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 4177-4179
  • 31
    • 79958189519 scopus 로고    scopus 로고
    • Despite the superior Michael acceptor ability of the nitroalkene and the well-documented synthetic utility of the nitro group; for selected reviews, see
    • Despite the superior Michael acceptor ability of the nitroalkene and the well-documented synthetic utility of the nitro group; for selected reviews, see
  • 33
    • 0003527998 scopus 로고    scopus 로고
    • Wiley-VCH, New York,; to our knowledge, only one single example has been reported about the intramolecular RC-type reaction of nitroalkenes, see reference [7])
    • N. Ono, The Nitro Group in Organic Synthesis, Wiley-VCH, New York, 2001; to our knowledge, only one single example has been reported about the intramolecular RC-type reaction of nitroalkenes, see reference [7]).
    • (2001) The Nitro Group in Organic Synthesis
    • Ono, N.1
  • 35
    • 36349033298 scopus 로고    scopus 로고
    • (Eds.: M. Christmann, S. Bräse), Wiley-VCH, Weinheim
    • Asymmetric Synthesis: The Essentials (Eds.:, M. Christmann, S. Bräse,), Wiley-VCH, Weinheim, 2007.
    • (2007) Asymmetric Synthesis: The Essentials
  • 36
  • 38
    • 0001176061 scopus 로고    scopus 로고
    • in (Eds. A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon, Oxford, p.
    • B. A. Keay, in Comprehensive Heterocyclic Chemistry II, Vol. 2 (Eds., A. R. Katritzky, C. W. Rees, E. F. V. Scriven,), Pergamon, Oxford, 1996, p. 395.
    • (1996) Comprehensive Heterocyclic Chemistry II, Vol. 2 , pp. 395
    • Keay, B.A.1
  • 48
    • 53549115929 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 5827-5829
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 5827-5829
  • 51
    • 79958228869 scopus 로고    scopus 로고
    • For recent reviews, see
    • For recent reviews, see
  • 57
    • 5344224096 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 4566-4583.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 4566-4583
  • 58
    • 79958216651 scopus 로고    scopus 로고
    • For selected examples, see
    • For selected examples, see
  • 66
    • 53549115888 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 5703-5705
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 5703-5705
  • 69
    • 33646573235 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 1952-1956
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 1952-1956
  • 74
    • 79958231997 scopus 로고    scopus 로고
    • For selected references, see
    • For selected references, see
  • 78
    • 78149445810 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 8379-8383
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 8379-8383
  • 80
    • 73249121389 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 9542-9545.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 9542-9545
  • 82
    • 55249110210 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 8703-8706
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 8703-8706
  • 84
  • 85
    • 79958216979 scopus 로고    scopus 로고
    • See the Supporting Information for more details on optimization of the conditions and synthetic transformations
    • See the Supporting Information for more details on optimization of the conditions and synthetic transformations.
  • 89
    • 79958194108 scopus 로고    scopus 로고
    • The configuration of 2 g was determined by X-ray crystallographic analysis. CCDC-763160 (2 g) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif
    • The configuration of 2 g was determined by X-ray crystallographic analysis. CCDC-763160 (2 g) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
  • 99
    • 79958195471 scopus 로고    scopus 로고
    • See the Supporting Information for more details on the proton-transfer reaction between the NuP and HBC, the solvent effect (using the PCM model) to the RC reaction, and the influence of a water molecule on the TS4
    • See the Supporting Information for more details on the proton-transfer reaction between the NuP and HBC, the solvent effect (using the PCM model) to the RC reaction, and the influence of a water molecule on the TS4.
  • 102
    • 79958209652 scopus 로고    scopus 로고
    • For selected examples of how water accelerated the rate of reaction, see
    • For selected examples of how water accelerated the rate of reaction, see
  • 104
    • 77956039300 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 6106-6110
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 6106-6110
  • 110
    • 79958191805 scopus 로고    scopus 로고
    • For selected examples, see
    • For selected examples, see
  • 116
    • 79958241476 scopus 로고    scopus 로고
    • A. L. Sabb, R. L. Vogel, G. P. Stack, D. A. Evrard, A. A. Failli, L. Krishnan, A. W. Chan, J. Ren, C. Guinosso, R. B. Baudy, J. Y.-C. Sze, Y. Li, Stanton III C. J., A. Nikitenko Wyeth Corp., New Jersey, PCT Int. Appl. WO 2006/089053
    • A. L. Sabb, R. L. Vogel, G. P. Stack, D. A. Evrard, A. A. Failli, L. Krishnan, A. W. Chan, J. Ren, C. Guinosso, R. B. Baudy, J. Y.-C. Sze, Y. Li, C. J. Stanton III, A. Nikitenko, Wyeth Corp., New Jersey, PCT Int. Appl. WO 2006/089053
  • 117
    • 38949115484 scopus 로고    scopus 로고
    • Chem. Abstr. 2006, 145, 271641
    • (2006) Chem. Abstr. , vol.145 , pp. 271641
  • 118
    • 79958242333 scopus 로고    scopus 로고
    • Glenmark Pharm. Ltd., Mumbai, PCT Int. Appl. WO 2005/033099
    • B. Gopalan, H. V. Joshi, D. M. Shah, S. R. Ghorpade, Glenmark Pharm. Ltd., Mumbai, PCT Int. Appl. WO 2005/033099.
    • Gopalan, B.1    Joshi, H.V.2    Shah, D.M.3    Ghorpade, S.R.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.