메뉴 건너뛰기




Volumn 36, Issue 4, 1997, Pages 371-374

First Examples of a Claisen Rearrangement Stereocontrolled by a Sulfinyl Group: Synthesis of Novel α-Sulfinyl Dithioesters

Author keywords

C C coupling; Chiral auxiliaries; Dithioesters rearrangements; Sulfoxides

Indexed keywords


EID: 0030895779     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199703711     Document Type: Article
Times cited : (30)

References (48)
  • 12
    • 0000447587 scopus 로고
    • J. K. Cha, S. C. Lewis, Tetrahedron Lett. 1984, 25, 5263-5266; M. J. Kurth, C.-M. Yu, ibid. 1984, 25, 5003-5006; S. Hatakeyama, K. Saijo, S. Takano, ibid. 1985, 26, 865-868; M. Balestra, J. Kallmerten, ibid. 1988, 29, 6901-6904; S. D. Kahn, W. J. Hehre, J. Org. Chem. 1988, 53, 301-305; R. Bruckner, H. Priepke, Angew. Chem. 1988, 100, 285-286; Angew. Chem. Int. Ed. Engl. 1988, 27, 278-279; S. Désert, P. Metzner, M. Ramdani, Tetrahedron 1992, 48, 10315-10326.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 5263-5266
    • Cha, J.K.1    Lewis, S.C.2
  • 13
    • 0343643361 scopus 로고
    • J. K. Cha, S. C. Lewis, Tetrahedron Lett. 1984, 25, 5263-5266; M. J. Kurth, C.-M. Yu, ibid. 1984, 25, 5003-5006; S. Hatakeyama, K. Saijo, S. Takano, ibid. 1985, 26, 865-868; M. Balestra, J. Kallmerten, ibid. 1988, 29, 6901-6904; S. D. Kahn, W. J. Hehre, J. Org. Chem. 1988, 53, 301-305; R. Bruckner, H. Priepke, Angew. Chem. 1988, 100, 285-286; Angew. Chem. Int. Ed. Engl. 1988, 27, 278-279; S. Désert, P. Metzner, M. Ramdani, Tetrahedron 1992, 48, 10315-10326.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 5003-5006
    • Kurth, M.J.1    Yu, C.-M.2
  • 14
    • 0021927694 scopus 로고
    • J. K. Cha, S. C. Lewis, Tetrahedron Lett. 1984, 25, 5263-5266; M. J. Kurth, C.-M. Yu, ibid. 1984, 25, 5003-5006; S. Hatakeyama, K. Saijo, S. Takano, ibid. 1985, 26, 865-868; M. Balestra, J. Kallmerten, ibid. 1988, 29, 6901-6904; S. D. Kahn, W. J. Hehre, J. Org. Chem. 1988, 53, 301-305; R. Bruckner, H. Priepke, Angew. Chem. 1988, 100, 285-286; Angew. Chem. Int. Ed. Engl. 1988, 27, 278-279; S. Désert, P. Metzner, M. Ramdani, Tetrahedron 1992, 48, 10315-10326.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 865-868
    • Hatakeyama, S.1    Saijo, K.2    Takano, S.3
  • 15
    • 1542482770 scopus 로고
    • J. K. Cha, S. C. Lewis, Tetrahedron Lett. 1984, 25, 5263-5266; M. J. Kurth, C.-M. Yu, ibid. 1984, 25, 5003-5006; S. Hatakeyama, K. Saijo, S. Takano, ibid. 1985, 26, 865-868; M. Balestra, J. Kallmerten, ibid. 1988, 29, 6901-6904; S. D. Kahn, W. J. Hehre, J. Org. Chem. 1988, 53, 301-305; R. Bruckner, H. Priepke, Angew. Chem. 1988, 100, 285-286; Angew. Chem. Int. Ed. Engl. 1988, 27, 278-279; S. Désert, P. Metzner, M. Ramdani, Tetrahedron 1992, 48, 10315-10326.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 6901-6904
    • Balestra, M.1    Kallmerten, J.2
  • 16
    • 0000431115 scopus 로고
    • J. K. Cha, S. C. Lewis, Tetrahedron Lett. 1984, 25, 5263-5266; M. J. Kurth, C.-M. Yu, ibid. 1984, 25, 5003-5006; S. Hatakeyama, K. Saijo, S. Takano, ibid. 1985, 26, 865-868; M. Balestra, J. Kallmerten, ibid. 1988, 29, 6901-6904; S. D. Kahn, W. J. Hehre, J. Org. Chem. 1988, 53, 301-305; R. Bruckner, H. Priepke, Angew. Chem. 1988, 100, 285-286; Angew. Chem. Int. Ed. Engl. 1988, 27, 278-279; S. Désert, P. Metzner, M. Ramdani, Tetrahedron 1992, 48, 10315-10326.
    • (1988) J. Org. Chem. , vol.53 , pp. 301-305
    • Kahn, S.D.1    Hehre, W.J.2
  • 17
    • 0000447587 scopus 로고
    • J. K. Cha, S. C. Lewis, Tetrahedron Lett. 1984, 25, 5263-5266; M. J. Kurth, C.-M. Yu, ibid. 1984, 25, 5003-5006; S. Hatakeyama, K. Saijo, S. Takano, ibid. 1985, 26, 865-868; M. Balestra, J. Kallmerten, ibid. 1988, 29, 6901-6904; S. D. Kahn, W. J. Hehre, J. Org. Chem. 1988, 53, 301-305; R. Bruckner, H. Priepke, Angew. Chem. 1988, 100, 285-286; Angew. Chem. Int. Ed. Engl. 1988, 27, 278-279; S. Désert, P. Metzner, M. Ramdani, Tetrahedron 1992, 48, 10315-10326.
    • (1988) Angew. Chem. , vol.100 , pp. 285-286
    • Bruckner, R.1    Priepke, H.2
  • 18
    • 84990166237 scopus 로고
    • J. K. Cha, S. C. Lewis, Tetrahedron Lett. 1984, 25, 5263-5266; M. J. Kurth, C.-M. Yu, ibid. 1984, 25, 5003-5006; S. Hatakeyama, K. Saijo, S. Takano, ibid. 1985, 26, 865-868; M. Balestra, J. Kallmerten, ibid. 1988, 29, 6901-6904; S. D. Kahn, W. J. Hehre, J. Org. Chem. 1988, 53, 301-305; R. Bruckner, H. Priepke, Angew. Chem. 1988, 100, 285-286; Angew. Chem. Int. Ed. Engl. 1988, 27, 278-279; S. Désert, P. Metzner, M. Ramdani, Tetrahedron 1992, 48, 10315-10326.
    • (1988) Angew. Chem. Int. Ed. Engl. , vol.27 , pp. 278-279
  • 19
    • 0026454348 scopus 로고
    • J. K. Cha, S. C. Lewis, Tetrahedron Lett. 1984, 25, 5263-5266; M. J. Kurth, C.-M. Yu, ibid. 1984, 25, 5003-5006; S. Hatakeyama, K. Saijo, S. Takano, ibid. 1985, 26, 865-868; M. Balestra, J. Kallmerten, ibid. 1988, 29, 6901-6904; S. D. Kahn, W. J. Hehre, J. Org. Chem. 1988, 53, 301-305; R. Bruckner, H. Priepke, Angew. Chem. 1988, 100, 285-286; Angew. Chem. Int. Ed. Engl. 1988, 27, 278-279; S. Désert, P. Metzner, M. Ramdani, Tetrahedron 1992, 48, 10315-10326.
    • (1992) Tetrahedron , vol.48 , pp. 10315-10326
    • Désert, S.1    Metzner, P.2    Ramdani, M.3
  • 21
    • 0025814902 scopus 로고
    • P. Beslin, S. Perrio, J. Chem. Soc. Chem. Commun. 1989, 414-416; Tetrahedron 1991, 47, 6275-6286.
    • (1991) Tetrahedron , vol.47 , pp. 6275-6286
  • 22
    • 37049098891 scopus 로고
    • R. C. Cookson, R. Gopalan, J. Chem. Soc. Chem. Commun. 1978, 608; G. H. Posner, R. D. Crouch, C. M. Kinter, J.-C. Carry, J. Org. Chem. 1991, 56, 6981-6987; J.-M. Vatèle, Tetrahedron Lett. 1983, 24, 1239-1242.
    • (1978) J. Chem. Soc. Chem. Commun. , pp. 608
    • Cookson, R.C.1    Gopalan, R.2
  • 23
    • 0001684281 scopus 로고
    • R. C. Cookson, R. Gopalan, J. Chem. Soc. Chem. Commun. 1978, 608; G. H. Posner, R. D. Crouch, C. M. Kinter, J.-C. Carry, J. Org. Chem. 1991, 56, 6981-6987; J.-M. Vatèle, Tetrahedron Lett. 1983, 24, 1239-1242.
    • (1991) J. Org. Chem. , vol.56 , pp. 6981-6987
    • Posner, G.H.1    Crouch, R.D.2    Kinter, C.M.3    Carry, J.-C.4
  • 24
    • 4243340894 scopus 로고
    • R. C. Cookson, R. Gopalan, J. Chem. Soc. Chem. Commun. 1978, 608; G. H. Posner, R. D. Crouch, C. M. Kinter, J.-C. Carry, J. Org. Chem. 1991, 56, 6981-6987; J.-M. Vatèle, Tetrahedron Lett. 1983, 24, 1239-1242.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 1239-1242
    • Vatèle, J.-M.1
  • 27
    • 84977296203 scopus 로고
    • P. J. W. Schuijl, L. Brandsma, Recl. Trav. Chim. Pays-Bas 1968, 87, 929-939; P. Metzner, T. N. Pham, J. Vialle, Nouv. J. Chim. 1978, 2, 179-182.
    • (1978) Nouv. J. Chim. , vol.2 , pp. 179-182
    • Metzner, P.1    Pham, T.N.2    Vialle, J.3
  • 29
    • 85077702395 scopus 로고
    • G. Solladié, Synthesis 1981, 185-196; C. Mioskowski, G. Solladié, Tetrahedron 1980, 36, 227-236.
    • (1981) Synthesis , pp. 185-196
    • Solladié, G.1
  • 32
    • 0345231116 scopus 로고
    • J.-C. Aloup, D. Farge, C. James, S. Mondot, I. Cavero, Drugs of the Future 1990, 15, 1098-1108; J.-C. Aloup, J. Bouchaudon, D. Farge, C. James, J. Deregnaucourt, M. Hardy-Louis, J. Med. Chem. 1987, 30, 24-29; M. Cinquini, A. Manfredi, H. Molinari, A. Restelli, Tetrahedron 1985, 41, 4929-4936.
    • (1990) Drugs of the Future , vol.15 , pp. 1098-1108
    • Aloup, J.-C.1    Farge, D.2    James, C.3    Mondot, S.4    Cavero, I.5
  • 34
    • 0006582405 scopus 로고
    • J.-C. Aloup, D. Farge, C. James, S. Mondot, I. Cavero, Drugs of the Future 1990, 15, 1098-1108; J.-C. Aloup, J. Bouchaudon, D. Farge, C. James, J. Deregnaucourt, M. Hardy-Louis, J. Med. Chem. 1987, 30, 24-29; M. Cinquini, A. Manfredi, H. Molinari, A. Restelli, Tetrahedron 1985, 41, 4929-4936.
    • (1985) Tetrahedron , vol.41 , pp. 4929-4936
    • Cinquini, M.1    Manfredi, A.2    Molinari, H.3    Restelli, A.4
  • 35
    • 85033150060 scopus 로고    scopus 로고
    • The designation cis refers to the relationship between the sulfinyl and the SLi groups
    • The designation cis refers to the relationship between the sulfinyl and the SLi groups.
  • 36
    • 85033146019 scopus 로고    scopus 로고
    • note
    • In previous work from our laboratories, we have demonstrated that enethiolate alkylation proceeded with complete retention of configuration [23]. The configurations of ketene dithioacetals were assigned based on the results of NOE difference studies, which were carried out on the corresponding S-benzyl ketene dithioacetals.
  • 37
    • 85033141537 scopus 로고    scopus 로고
    • note
    • 1HNMR signals of the MeS groups and by measuring the integrals of both singlets.
  • 38
    • 85033132222 scopus 로고    scopus 로고
    • note
    • w = 0.0574). Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-179-147. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: Int. code +(1223) 336-033: e-mail: deposit@chemcrys.cam.ac.uk).
  • 39
    • 85033155945 scopus 로고    scopus 로고
    • note
    • Systematic investigation of NMR spectra shows that the chemical shifts of the proton linked to the stereogenic center and of the MeS group of the minor isomer occur downfield relative to that of the major isomer.
  • 40
    • 0002451214 scopus 로고
    • N. T. Anh, O. Eisenstein, Nouv. J. Chim. 1977, 1, 61-70; N. T. Anh, F. Maurel, J.-M. Lefour, New J. Chem. 1995, 19, 353-364; N. T. Anh, Orbitales frontières - Manuel pratique, InterEditions CNRS Editions, Paris, 1995.
    • (1977) Nouv. J. Chim. , vol.1 , pp. 61-70
    • Anh, N.T.1    Eisenstein, O.2
  • 41
    • 0000970039 scopus 로고
    • N. T. Anh, O. Eisenstein, Nouv. J. Chim. 1977, 1, 61-70; N. T. Anh, F. Maurel, J.-M. Lefour, New J. Chem. 1995, 19, 353-364; N. T. Anh, Orbitales frontières - Manuel pratique, InterEditions CNRS Editions, Paris, 1995.
    • (1995) New J. Chem. , vol.19 , pp. 353-364
    • Anh, N.T.1    Maurel, F.2    Lefour, J.-M.3
  • 42
    • 0010370765 scopus 로고
    • InterEditions CNRS Editions, Paris
    • N. T. Anh, O. Eisenstein, Nouv. J. Chim. 1977, 1, 61-70; N. T. Anh, F. Maurel, J.-M. Lefour, New J. Chem. 1995, 19, 353-364; N. T. Anh, Orbitales frontières - Manuel pratique, InterEditions CNRS Editions, Paris, 1995.
    • (1995) Orbitales Frontières - Manuel Pratique
    • Anh, N.T.1
  • 44
    • 85033154038 scopus 로고    scopus 로고
    • note
    • 2 = H) containing predominantly the E isomer show that there is an independency between the configuration of the ketene dithioacetal and rearrangement selectivity (cf. ref. [6]).
  • 45
    • 84981574529 scopus 로고
    • A. W Herriott, D. Picker, Synthesis 1975, 447-448; C. R. Johnson, J. E. Keiser, Org. Synth. 1966, 46, 78-80.
    • (1975) Synthesis , pp. 447-448
    • Herriott, A.W.1    Picker, D.2
  • 46
    • 0002008049 scopus 로고
    • A. W Herriott, D. Picker, Synthesis 1975, 447-448; C. R. Johnson, J. E. Keiser, Org. Synth. 1966, 46, 78-80.
    • (1966) Org. Synth. , vol.46 , pp. 78-80
    • Johnson, C.R.1    Keiser, J.E.2
  • 48
    • 0001311326 scopus 로고
    • P. Beslin, P. Metzner, Y. Vallée, J. Vialle, Tetrahedron Lett. 1983, 24, 3617-3620; P. Beslin, Y. Vallée, Tetrahedron 1985, 41, 2691-2705.
    • (1985) Tetrahedron , vol.41 , pp. 2691-2705
    • Beslin, P.1    Vallée, Y.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.