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Volumn 3, Issue 9, 1997, Pages 1472-1481

Chiral Lewis acid controlled synthesis (CLAC synthesis): Chiral Lewis acids influence the reaction course in asymmetric aldol reactions for the synthesis of enantiomeric dihydroxythioester derivatives in the presence of chiral diamines derived from L-proline

Author keywords

Aldol reactions; Assymetric synthesis; Diamines; Enatioselective synthesis; Lewis acids

Indexed keywords


EID: 0030776295     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970030914     Document Type: Article
Times cited : (47)

References (76)
  • 7
    • 0000048258 scopus 로고
    • Eds.: B. M. Trost, I. Fleming, Pergamon, Oxford
    • c) W. Oppolzer, in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 315-399;
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 315-399
    • Oppolzer, W.1
  • 12
    • 0000584420 scopus 로고
    • Ed.: J. D. Morrison, Academic Press, New York
    • a) C. H. Heathcock, in Asymmetric Synthesis, Vol. 3 (Ed.: J. D. Morrison), Academic Press, New York, 1984, p. 111-212;
    • (1984) Asymmetric Synthesis , vol.3 , pp. 111-212
    • Heathcock, C.H.1
  • 15
    • 0000851696 scopus 로고
    • Eds.: B. M. Trost, I. Fleming, Pergamon, Oxford
    • d) C. H. Heathcock, in Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 133-179;
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 133-179
    • Heathcock, C.H.1
  • 20
    • 0000922736 scopus 로고    scopus 로고
    • Eds.: G. Helmchen, R. W. Hoffmann, J. Mutzer, E. Schaumann, Thieme, Stuttgart
    • i) M. Braun, in Stereoselective Synthesis, Vol. 3 (Eds.: G. Helmchen, R. W. Hoffmann, J. Mutzer, E. Schaumann), Thieme, Stuttgart, 1996, p. 1603.
    • (1996) Stereoselective Synthesis , vol.3 , pp. 1603
    • Braun, M.1
  • 21
    • 0028151214 scopus 로고
    • This means that reports on asymmetric synthesis of both syn- and anti-aldol adducts from the same starting materials are rare. The preparation of syn- and anti-aldol adducts from boron enolates of α′-alkoxy ketones by choosing protective groups for the alkoxy groups has been reported: a) I. Paterson, D. J. Wallace, M. Velázquez, Tetrahedron Lett. 1994, 35, 9083-9086; see also b) D. A. Evans, M. G. Yang, M. J. Dart, J. L. Duffy, A. S. Kim, J. Am. Chem. Soc. 1995, 117, 9598-9599.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 9083-9086
    • Paterson, I.1    Wallace, D.J.2    Velázquez, M.3
  • 22
    • 0001051059 scopus 로고
    • This means that reports on asymmetric synthesis of both syn- and anti-aldol adducts from the same starting materials are rare. The preparation of syn- and anti-aldol adducts from boron enolates of α′-alkoxy ketones by choosing protective groups for the alkoxy groups has been reported: a) I. Paterson, D. J. Wallace, M. Velázquez, Tetrahedron Lett. 1994, 35, 9083-9086; see also b) D. A. Evans, M. G. Yang, M. J. Dart, J. L. Duffy, A. S. Kim, J. Am. Chem. Soc. 1995, 117, 9598-9599.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 9598-9599
    • Evans, D.A.1    Yang, M.G.2    Dart, M.J.3    Duffy, J.L.4    Kim, A.S.5
  • 24
    • 0000530344 scopus 로고
    • Eds.: B. M. Trost, I. Fleming, Pergamon, Oxford
    • b) M. Yamaguchi, in Comprehensive Organic Synthesis, Vol. 1 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 325-353;
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 325-353
    • Yamaguchi, M.1
  • 32
    • 0028898190 scopus 로고
    • Based on this idea, both diastereomers were prepared in high optical purities. For preliminary communications, see a) S. Kobayashi, T. Hayashi, J. Org. Chem. 1995, 60, 1098-1099; b) S. Kobayashi, M. Horibe, M. Matsumura, Synlett 1995, 675-676; c) S. Kobayashi, M. Horibe, Chem. Lett. 1995, 1029-1030.
    • (1995) J. Org. Chem. , vol.60 , pp. 1098-1099
    • Kobayashi, S.1    Hayashi, T.2
  • 33
    • 0028898190 scopus 로고
    • Based on this idea, both diastereomers were prepared in high optical purities. For preliminary communications, see a) S. Kobayashi, T. Hayashi, J. Org. Chem. 1995, 60, 1098-1099; b) S. Kobayashi, M. Horibe, M. Matsumura, Synlett 1995, 675-676; c) S. Kobayashi, M. Horibe, Chem. Lett. 1995, 1029-1030.
    • (1995) Synlett , vol.675-676
    • Kobayashi, S.1    Horibe, M.2    Matsumura, M.3
  • 34
    • 0028898190 scopus 로고
    • Based on this idea, both diastereomers were prepared in high optical purities. For preliminary communications, see a) S. Kobayashi, T. Hayashi, J. Org. Chem. 1995, 60, 1098-1099; b) S. Kobayashi, M. Horibe, M. Matsumura, Synlett 1995, 675-676; c) S. Kobayashi, M. Horibe, Chem. Lett. 1995, 1029-1030.
    • (1995) Chem. Lett. , pp. 1029-1030
    • Kobayashi, S.1    Horibe, M.2
  • 35
    • 0347591023 scopus 로고
    • a) S. C. Stinson, Chem. Eng. News 1995, Oct. 9, 44-74; 1993, Sept. 27, 38-65;
    • (1995) Chem. Eng. News , vol.OCT. 9 , pp. 44-74
    • Stinson, S.C.1
  • 36
    • 0347591023 scopus 로고
    • a) S. C. Stinson, Chem. Eng. News 1995, Oct. 9, 44-74; 1993, Sept. 27, 38-65;
    • (1993) Chem. Eng. News , vol.SEPT. 27 , pp. 38-65
  • 38
    • 0001045470 scopus 로고
    • c) quite recently, we developed a new method for preparation of both enantiomers from a single chiral source and a choice of achiral ligands in the chiral lanthanide(III)-catalyzed Diels-Alder reactions. S. Kobayashi, H. Ishitani, J. Am. Chem. Soc. 1994, 116, 4083-4084; S. Kobayashi, H. Ishitani, I. Hachiya, M. Araki, Tetrahedron 1994, 50, 11623-11636.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 4083-4084
    • Kobayashi, S.1    Ishitani, H.2
  • 39
    • 0027963432 scopus 로고
    • c) quite recently, we developed a new method for preparation of both enantiomers from a single chiral source and a choice of achiral ligands in the chiral lanthanide(III)-catalyzed Diels-Alder reactions. S. Kobayashi, H. Ishitani, J. Am. Chem. Soc. 1994, 116, 4083-4084; S. Kobayashi, H. Ishitani, I. Hachiya, M. Araki, Tetrahedron 1994, 50, 11623-11636.
    • (1994) Tetrahedron , vol.50 , pp. 11623-11636
    • Kobayashi, S.1    Ishitani, H.2    Hachiya, I.3    Araki, M.4
  • 44
    • 33748238772 scopus 로고
    • For chiral Lewis acid promoted aldol reactions of silyl enolates with aldehydes, see T. Bach, Angew. Chem. Int. Ed. Engl. 1994, 33, 417-419.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 417-419
    • Bach, T.1
  • 51
    • 0039204420 scopus 로고
    • Fujitsu, Tokyo
    • Calculated with MOPAC93 using the PM3 hamiltonian. J. J. P. Stewart, MOPAC93.00 Manual; Fujitsu, Tokyo, 1993.
    • (1993) MOPAC93.00 Manual
    • Stewart, J.J.P.1
  • 52
    • 0028966866 scopus 로고
    • The reaction of (E)-1-ethylthio-1-(trimethylsiloxy)-2-(tert-butyldimethylsiloxy)ethene with benzaldehyde was sluggish under the same reaction conditions. Cf. ref. [2]. See also S. Kobayashi, M. Horibe, I. Hachiya, Tetrahedron Lett. 1995, 36, 3173-3176.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 3173-3176
    • Kobayashi, S.1    Horibe, M.2    Hachiya, I.3
  • 53
    • 0000472173 scopus 로고
    • In some cycloaddition or cross-coupling reactions, it was reported that the stereochemical course changed using chiral sources with same configurations and slightly different structures, but the selectivities were moderate: a) K. Ishihara, Q. Gao, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10412-10413; b) T. Hayashi, M. Konishi, M. Fukushima, T. Mise, M. Kagotani, M. Tajika, M. Kumada, ibid. 1982, 104, 180-186; cf. c) H. Suzuki, K. Mochizuki, T. Hattori, N. Takahashi, O. Tajima, T. Takiguchi, Bull. Chem. Soc. Jpn. 1988, 61, 1999-2005.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 10412-10413
    • Ishihara, K.1    Gao, Q.2    Yamamoto, H.3
  • 54
    • 0001717911 scopus 로고
    • In some cycloaddition or cross-coupling reactions, it was reported that the stereochemical course changed using chiral sources with same configurations and slightly different structures, but the selectivities were moderate: a) K. Ishihara, Q. Gao, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10412-10413; b) T. Hayashi, M. Konishi, M. Fukushima, T. Mise, M. Kagotani, M. Tajika, M. Kumada, ibid. 1982, 104, 180-186; cf. c) H. Suzuki, K. Mochizuki, T. Hattori, N. Takahashi, O. Tajima, T. Takiguchi, Bull. Chem. Soc. Jpn. 1988, 61, 1999-2005.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 180-186
    • Hayashi, T.1    Konishi, M.2    Fukushima, M.3    Mise, T.4    Kagotani, M.5    Tajika, M.6    Kumada, M.7
  • 55
    • 0023729131 scopus 로고
    • In some cycloaddition or cross-coupling reactions, it was reported that the stereochemical course changed using chiral sources with same configurations and slightly different structures, but the selectivities were moderate: a) K. Ishihara, Q. Gao, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10412-10413; b) T. Hayashi, M. Konishi, M. Fukushima, T. Mise, M. Kagotani, M. Tajika, M. Kumada, ibid. 1982, 104, 180-186; cf. c) H. Suzuki, K. Mochizuki, T. Hattori, N. Takahashi, O. Tajima, T. Takiguchi, Bull. Chem. Soc. Jpn. 1988, 61, 1999-2005.
    • (1988) Bull. Chem. Soc. Jpn. , vol.61 , pp. 1999-2005
    • Suzuki, H.1    Mochizuki, K.2    Hattori, T.3    Takahashi, N.4    Tajima, O.5    Takiguchi, T.6
  • 57
    • 4444276636 scopus 로고
    • For preparation of optically active 1,2-diols using the osmium-catalyzed asymmetric dihydroxylation, see a) H. C. Kolb, M. S. Van Nieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547; b) R. A. Johnson, K. B. Sharpless, Catalytic Asymmetric Dihydroxylation, in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, Weinheim, 1993, pp. 227-272, and references cited therein.
    • (1994) Chem. Rev. , vol.94 , pp. 2483-2547
    • Kolb, H.C.1    Van Nieuwenhze, M.S.2    Sharpless, K.B.3
  • 58
    • 4444276636 scopus 로고
    • Catalytic Asymmetric Dihydroxylation
    • Ed.: I. Ojima, VCH, Weinheim, and references cited therein
    • For preparation of optically active 1,2-diols using the osmium-catalyzed asymmetric dihydroxylation, see a) H. C. Kolb, M. S. Van Nieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547; b) R. A. Johnson, K. B. Sharpless, Catalytic Asymmetric Dihydroxylation, in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, Weinheim, 1993, pp. 227-272, and references cited therein.
    • (1993) Catalytic Asymmetric Synthesis , pp. 227-272
    • Johnson, R.A.1    Sharpless, K.B.2
  • 69
    • 0001911287 scopus 로고
    • b) R. W. Stevens, T. Mukaiyama, Chem. Lett. 1983, 1799-1802. There are four possible conformational isomers of bicyclo[3.3.0]octane-like structure (see below). I and IV are the more stable because there are steric repulsions between hydrogen atoms in II and III. (Equation Presented)
    • (1983) Chem. Lett. , pp. 1799-1802
    • Stevens, R.W.1    Mukaiyama, T.2
  • 70
    • 0342517587 scopus 로고    scopus 로고
    • note
    • 5CN at -78°C.) (Equation Presented)


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