메뉴 건너뛰기




Volumn 58, Issue 41, 2002, Pages 8331-8339

Asymmetric aldol reaction of enol trichloroacetate catalyzed by tin methoxide and BINAP·silver(I) complex

Author keywords

Aldehyde; Asymmetric aldol reaction; BINAP silver(I) complex; Diketene; Enol trichloroacetate; Tin methoxide

Indexed keywords

ACETIC ACID DERIVATIVE; ALKENE DERIVATIVE; BENZALDEHYDE; CYCLOHEXANONE; ENOL TRICHLOROACETATE; SILVER DERIVATIVE; TIN DERIVATIVE; TRIBUTYLTIN METHOXIDE; UNCLASSIFIED DRUG;

EID: 0037037982     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00984-5     Document Type: Article
Times cited : (38)

References (68)
  • 2
    • 0004063249 scopus 로고    scopus 로고
    • Weinheim: VCH
    • Reviews: (a) Pereyre M., Quintard J.-P., Rahm A. Tin in Organic Synthesis. 1987;Butterworths, London. p 286 (b) Davies A.G. Organotin Chemistry. 1997;VCH, Weinheim. p 185.
    • (1997) Organotin Chemistry , pp. 185
    • Davies, A.G.1
  • 12
    • 0000851696 scopus 로고
    • B.M. Trost, I. Fleming, & C.H. Heathcock. Oxford: Pergamon. and related chapters
    • Review: (a) Heathcock C.H. Trost B.M., Fleming I., Heathcock C.H., Comprehensive Organic Synthesis. Vol. 2:1991;Pergamon, Oxford. p 133 and related chapters (b) Braun M. Helmchen G., Hoffmann R.W., Mulzer J., Schaumann E., Houben-Weyl: Methods of Organic Chemistry. Vol. E 21:1995;Georg Thieme Verlag, Stuttgart. p 1603.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 133
    • Heathcock, C.H.1
  • 13
    • 0001524205 scopus 로고
    • G. Helmchen, R.W. Hoffmann, J. Mulzer, & E. Schaumann. Stuttgart: Georg Thieme Verlag
    • Review: (a) Heathcock C.H. Trost B.M., Fleming I., Heathcock C.H., Comprehensive Organic Synthesis. Vol. 2:1991;Pergamon, Oxford. p 133 and related chapters (b) Braun M. Helmchen G., Hoffmann R.W., Mulzer J., Schaumann E., Houben-Weyl: Methods of Organic Chemistry. Vol. E 21:1995;Georg Thieme Verlag, Stuttgart. p 1603.
    • (1995) Houben-Weyl: Methods of Organic Chemistry , vol.E 21 , pp. 1603
    • Braun, M.1
  • 24
    • 0001316868 scopus 로고
    • B.M. Trost, I. Fleming, & C.H. Heathcock. Oxford: Pergamon
    • Review: Gennari C. Trost B.M., Fleming I., Heathcock C.H., Comprehensive Organic Synthesis. Vol. 2:1991;629 Pergamon, Oxford.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 629
    • Gennari, C.1
  • 27
    • 0011196156 scopus 로고
    • Methyl trichloroacetate has been reported to be hydrolyzed in aqueous alkaline solution faster than methyl acetate, see: Barthel J., Bäder G., Schmeer G. Z. Phys. Chem. 62:1968;63.
    • (1968) Z. Phys. Chem. , vol.62 , pp. 63
    • Barthel, J.1    Bäder, G.2    Schmeer, G.3
  • 35
    • 33748238772 scopus 로고
    • Reviews for catalytic asymmetric aldol reactions using silyl enol ethers or ketene silyl acetals: (a) Bach T. Angew. Chem. Int. Ed. Engl. 33:1994;417 (b) Hollis T.K., Bosnich B. J. Am. Chem. Soc. 117:1995;4570 (c) Braun M. Helmchen G., Hoffmann R.W., Mulzer J., Schaumann E., Houben-Weyl: Methods of Organic Chemistry. Vol. E 21:1995;1730 Georg Thieme Verlag, Stuttgart, (d) Nelson S.G. Tetrahedron: Asymmetry. 9:1998;357 (e) Gröger H., Vogl E.M., Shibasaki M. Chem. Eur. J. 4:1998;1137 (f) Mahrwald R. Chem. Rev. 99:1999;1095 (g) Carreira E.M. Jacobsen E.N., Pfaltz A., Yamamoto H., Comprehensive Asymmetric Catalysis. Vol. 3:1999;997 Springer, Heidelberg, (h) Arya P., Qin H. Tetrahedron. 56:2000;917 (i) Machajewski T.D., Wong C.-H. Angew. Chem. Int. Ed. 39:2000;1352 (j) Carreira E.M. Otera J., Modern Carbonyl Chemistry. 2000;227 Wiley-VCH, Weinheim. Chapter 8 (k) Yamamoto H., Lewis Acids in Organic Synthesis. Vols. 1 and 2:2000;Wiley-VCH, Weinheim.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 417
    • Bach, T.1
  • 36
    • 1542520958 scopus 로고
    • Reviews for catalytic asymmetric aldol reactions using silyl enol ethers or ketene silyl acetals: (a) Bach T. Angew. Chem. Int. Ed. Engl. 33:1994;417 (b) Hollis T.K., Bosnich B. J. Am. Chem. Soc. 117:1995;4570 (c) Braun M. Helmchen G., Hoffmann R.W., Mulzer J., Schaumann E., Houben-Weyl: Methods of Organic Chemistry. Vol. E 21:1995;1730 Georg Thieme Verlag, Stuttgart, (d) Nelson S.G. Tetrahedron: Asymmetry. 9:1998;357 (e) Gröger H., Vogl E.M., Shibasaki M. Chem. Eur. J. 4:1998;1137 (f) Mahrwald R. Chem. Rev. 99:1999;1095 (g) Carreira E.M. Jacobsen E.N., Pfaltz A., Yamamoto H., Comprehensive Asymmetric Catalysis. Vol. 3:1999;997 Springer, Heidelberg, (h) Arya P., Qin H. Tetrahedron. 56:2000;917 (i) Machajewski T.D., Wong C.-H. Angew. Chem. Int. Ed. 39:2000;1352 (j) Carreira E.M. Otera J., Modern Carbonyl Chemistry. 2000;227 Wiley-VCH, Weinheim. Chapter 8 (k) Yamamoto H., Lewis Acids in Organic Synthesis. Vols. 1 and 2:2000;Wiley-VCH, Weinheim.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 4570
    • Hollis, T.K.1    Bosnich, B.2
  • 37
    • 0000490738 scopus 로고
    • G. Helmchen, R.W. Hoffmann, J. Mulzer, & E. Schaumann. Georg Thieme Verlag: Stuttgart
    • Reviews for catalytic asymmetric aldol reactions using silyl enol ethers or ketene silyl acetals: (a) Bach T. Angew. Chem. Int. Ed. Engl. 33:1994;417 (b) Hollis T.K., Bosnich B. J. Am. Chem. Soc. 117:1995;4570 (c) Braun M. Helmchen G., Hoffmann R.W., Mulzer J., Schaumann E., Houben-Weyl: Methods of Organic Chemistry. Vol. E 21:1995;1730 Georg Thieme Verlag, Stuttgart, (d) Nelson S.G. Tetrahedron: Asymmetry. 9:1998;357 (e) Gröger H., Vogl E.M., Shibasaki M. Chem. Eur. J. 4:1998;1137 (f) Mahrwald R. Chem. Rev. 99:1999;1095 (g) Carreira E.M. Jacobsen E.N., Pfaltz A., Yamamoto H., Comprehensive Asymmetric Catalysis. Vol. 3:1999;997 Springer, Heidelberg, (h) Arya P., Qin H. Tetrahedron. 56:2000;917 (i) Machajewski T.D., Wong C.-H. Angew. Chem. Int. Ed. 39:2000;1352 (j) Carreira E.M. Otera J., Modern Carbonyl Chemistry. 2000;227 Wiley-VCH, Weinheim. Chapter 8 (k) Yamamoto H., Lewis Acids in Organic Synthesis. Vols. 1 and 2:2000;Wiley-VCH, Weinheim.
    • (1995) Houben-Weyl: Methods of Organic Chemistry , vol.E 21 , pp. 1730
    • Braun, M.1
  • 38
    • 0032512595 scopus 로고    scopus 로고
    • Reviews for catalytic asymmetric aldol reactions using silyl enol ethers or ketene silyl acetals: (a) Bach T. Angew. Chem. Int. Ed. Engl. 33:1994;417 (b) Hollis T.K., Bosnich B. J. Am. Chem. Soc. 117:1995;4570 (c) Braun M. Helmchen G., Hoffmann R.W., Mulzer J., Schaumann E., Houben-Weyl: Methods of Organic Chemistry. Vol. E 21:1995;1730 Georg Thieme Verlag, Stuttgart, (d) Nelson S.G. Tetrahedron: Asymmetry. 9:1998;357 (e) Gröger H., Vogl E.M., Shibasaki M. Chem. Eur. J. 4:1998;1137 (f) Mahrwald R. Chem. Rev. 99:1999;1095 (g) Carreira E.M. Jacobsen E.N., Pfaltz A., Yamamoto H., Comprehensive Asymmetric Catalysis. Vol. 3:1999;997 Springer, Heidelberg, (h) Arya P., Qin H. Tetrahedron. 56:2000;917 (i) Machajewski T.D., Wong C.-H. Angew. Chem. Int. Ed. 39:2000;1352 (j) Carreira E.M. Otera J., Modern Carbonyl Chemistry. 2000;227 Wiley-VCH, Weinheim. Chapter 8 (k) Yamamoto H., Lewis Acids in Organic Synthesis. Vols. 1 and 2:2000;Wiley-VCH, Weinheim.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 357
    • Nelson, S.G.1
  • 39
    • 0031849225 scopus 로고    scopus 로고
    • Reviews for catalytic asymmetric aldol reactions using silyl enol ethers or ketene silyl acetals: (a) Bach T. Angew. Chem. Int. Ed. Engl. 33:1994;417 (b) Hollis T.K., Bosnich B. J. Am. Chem. Soc. 117:1995;4570 (c) Braun M. Helmchen G., Hoffmann R.W., Mulzer J., Schaumann E., Houben-Weyl: Methods of Organic Chemistry. Vol. E 21:1995;1730 Georg Thieme Verlag, Stuttgart, (d) Nelson S.G. Tetrahedron: Asymmetry. 9:1998;357 (e) Gröger H., Vogl E.M., Shibasaki M. Chem. Eur. J. 4:1998;1137 (f) Mahrwald R. Chem. Rev. 99:1999;1095 (g) Carreira E.M. Jacobsen E.N., Pfaltz A., Yamamoto H., Comprehensive Asymmetric Catalysis. Vol. 3:1999;997 Springer, Heidelberg, (h) Arya P., Qin H. Tetrahedron. 56:2000;917 (i) Machajewski T.D., Wong C.-H. Angew. Chem. Int. Ed. 39:2000;1352 (j) Carreira E.M. Otera J., Modern Carbonyl Chemistry. 2000;227 Wiley-VCH, Weinheim. Chapter 8 (k) Yamamoto H., Lewis Acids in Organic Synthesis. Vols. 1 and 2:2000;Wiley-VCH, Weinheim.
    • (1998) Chem. Eur. J. , vol.4 , pp. 1137
    • Gröger, H.1    Vogl, E.M.2    Shibasaki, M.3
  • 40
    • 0001196589 scopus 로고    scopus 로고
    • Reviews for catalytic asymmetric aldol reactions using silyl enol ethers or ketene silyl acetals: (a) Bach T. Angew. Chem. Int. Ed. Engl. 33:1994;417 (b) Hollis T.K., Bosnich B. J. Am. Chem. Soc. 117:1995;4570 (c) Braun M. Helmchen G., Hoffmann R.W., Mulzer J., Schaumann E., Houben-Weyl: Methods of Organic Chemistry. Vol. E 21:1995;1730 Georg Thieme Verlag, Stuttgart, (d) Nelson S.G. Tetrahedron: Asymmetry. 9:1998;357 (e) Gröger H., Vogl E.M., Shibasaki M. Chem. Eur. J. 4:1998;1137 (f) Mahrwald R. Chem. Rev. 99:1999;1095 (g) Carreira E.M. Jacobsen E.N., Pfaltz A., Yamamoto H., Comprehensive Asymmetric Catalysis. Vol. 3:1999;997 Springer, Heidelberg, (h) Arya P., Qin H. Tetrahedron. 56:2000;917 (i) Machajewski T.D., Wong C.-H. Angew. Chem. Int. Ed. 39:2000;1352 (j) Carreira E.M. Otera J., Modern Carbonyl Chemistry. 2000;227 Wiley-VCH, Weinheim. Chapter 8 (k) Yamamoto H., Lewis Acids in Organic Synthesis. Vols. 1 and 2:2000;Wiley-VCH, Weinheim.
    • (1999) Chem. Rev. , vol.99 , pp. 1095
    • Mahrwald, R.1
  • 41
    • 0000699983 scopus 로고    scopus 로고
    • E.N. Jacobsen, A. Pfaltz, & H. Yamamoto. Springer: Heidelberg
    • Reviews for catalytic asymmetric aldol reactions using silyl enol ethers or ketene silyl acetals: (a) Bach T. Angew. Chem. Int. Ed. Engl. 33:1994;417 (b) Hollis T.K., Bosnich B. J. Am. Chem. Soc. 117:1995;4570 (c) Braun M. Helmchen G., Hoffmann R.W., Mulzer J., Schaumann E., Houben-Weyl: Methods of Organic Chemistry. Vol. E 21:1995;1730 Georg Thieme Verlag, Stuttgart, (d) Nelson S.G. Tetrahedron: Asymmetry. 9:1998;357 (e) Gröger H., Vogl E.M., Shibasaki M. Chem. Eur. J. 4:1998;1137 (f) Mahrwald R. Chem. Rev. 99:1999;1095 (g) Carreira E.M. Jacobsen E.N., Pfaltz A., Yamamoto H., Comprehensive Asymmetric Catalysis. Vol. 3:1999;997 Springer, Heidelberg, (h) Arya P., Qin H. Tetrahedron. 56:2000;917 (i) Machajewski T.D., Wong C.-H. Angew. Chem. Int. Ed. 39:2000;1352 (j) Carreira E.M. Otera J., Modern Carbonyl Chemistry. 2000;227 Wiley-VCH, Weinheim. Chapter 8 (k) Yamamoto H., Lewis Acids in Organic Synthesis. Vols. 1 and 2:2000;Wiley-VCH, Weinheim.
    • (1999) Comprehensive Asymmetric Catalysis , vol.3 , pp. 997
    • Carreira, E.M.1
  • 42
    • 0034635481 scopus 로고    scopus 로고
    • Reviews for catalytic asymmetric aldol reactions using silyl enol ethers or ketene silyl acetals: (a) Bach T. Angew. Chem. Int. Ed. Engl. 33:1994;417 (b) Hollis T.K., Bosnich B. J. Am. Chem. Soc. 117:1995;4570 (c) Braun M. Helmchen G., Hoffmann R.W., Mulzer J., Schaumann E., Houben-Weyl: Methods of Organic Chemistry. Vol. E 21:1995;1730 Georg Thieme Verlag, Stuttgart, (d) Nelson S.G. Tetrahedron: Asymmetry. 9:1998;357 (e) Gröger H., Vogl E.M., Shibasaki M. Chem. Eur. J. 4:1998;1137 (f) Mahrwald R. Chem. Rev. 99:1999;1095 (g) Carreira E.M. Jacobsen E.N., Pfaltz A., Yamamoto H., Comprehensive Asymmetric Catalysis. Vol. 3:1999;997 Springer, Heidelberg, (h) Arya P., Qin H. Tetrahedron. 56:2000;917 (i) Machajewski T.D., Wong C.-H. Angew. Chem. Int. Ed. 39:2000;1352 (j) Carreira E.M. Otera J., Modern Carbonyl Chemistry. 2000;227 Wiley-VCH, Weinheim. Chapter 8 (k) Yamamoto H., Lewis Acids in Organic Synthesis. Vols. 1 and 2:2000;Wiley-VCH, Weinheim.
    • (2000) Tetrahedron , vol.56 , pp. 917
    • Arya, P.1    Qin, H.2
  • 43
    • 0034678591 scopus 로고    scopus 로고
    • Reviews for catalytic asymmetric aldol reactions using silyl enol ethers or ketene silyl acetals: (a) Bach T. Angew. Chem. Int. Ed. Engl. 33:1994;417 (b) Hollis T.K., Bosnich B. J. Am. Chem. Soc. 117:1995;4570 (c) Braun M. Helmchen G., Hoffmann R.W., Mulzer J., Schaumann E., Houben-Weyl: Methods of Organic Chemistry. Vol. E 21:1995;1730 Georg Thieme Verlag, Stuttgart, (d) Nelson S.G. Tetrahedron: Asymmetry. 9:1998;357 (e) Gröger H., Vogl E.M., Shibasaki M. Chem. Eur. J. 4:1998;1137 (f) Mahrwald R. Chem. Rev. 99:1999;1095 (g) Carreira E.M. Jacobsen E.N., Pfaltz A., Yamamoto H., Comprehensive Asymmetric Catalysis. Vol. 3:1999;997 Springer, Heidelberg, (h) Arya P., Qin H. Tetrahedron. 56:2000;917 (i) Machajewski T.D., Wong C.-H. Angew. Chem. Int. Ed. 39:2000;1352 (j) Carreira E.M. Otera J., Modern Carbonyl Chemistry. 2000;227 Wiley-VCH, Weinheim. Chapter 8 (k) Yamamoto H., Lewis Acids in Organic Synthesis. Vols. 1 and 2:2000;Wiley-VCH, Weinheim.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 1352
    • Machajewski, T.D.1    Wong, C.-H.2
  • 44
    • 0011233023 scopus 로고    scopus 로고
    • Weinheim: Wiley-VCH Chapter 8
    • Reviews for catalytic asymmetric aldol reactions using silyl enol ethers or ketene silyl acetals: (a) Bach T. Angew. Chem. Int. Ed. Engl. 33:1994;417 (b) Hollis T.K., Bosnich B. J. Am. Chem. Soc. 117:1995;4570 (c) Braun M. Helmchen G., Hoffmann R.W., Mulzer J., Schaumann E., Houben-Weyl: Methods of Organic Chemistry. Vol. E 21:1995;1730 Georg Thieme Verlag, Stuttgart, (d) Nelson S.G. Tetrahedron: Asymmetry. 9:1998;357 (e) Gröger H., Vogl E.M., Shibasaki M. Chem. Eur. J. 4:1998;1137 (f) Mahrwald R. Chem. Rev. 99:1999;1095 (g) Carreira E.M. Jacobsen E.N., Pfaltz A., Yamamoto H., Comprehensive Asymmetric Catalysis. Vol. 3:1999;997 Springer, Heidelberg, (h) Arya P., Qin H. Tetrahedron. 56:2000;917 (i) Machajewski T.D., Wong C.-H. Angew. Chem. Int. Ed. 39:2000;1352 (j) Carreira E.M. Otera J., Modern Carbonyl Chemistry. 2000;227 Wiley-VCH, Weinheim. Chapter 8 (k) Yamamoto H., Lewis Acids in Organic Synthesis. Vols. 1 and 2:2000;Wiley-VCH, Weinheim.
    • (2000) Modern Carbonyl Chemistry , pp. 227
    • Carreira, E.M.1    Otera, J.2
  • 45
    • 84955394357 scopus 로고    scopus 로고
    • Weinheim: Wiley-VCH
    • Reviews for catalytic asymmetric aldol reactions using silyl enol ethers or ketene silyl acetals: (a) Bach T. Angew. Chem. Int. Ed. Engl. 33:1994;417 (b) Hollis T.K., Bosnich B. J. Am. Chem. Soc. 117:1995;4570 (c) Braun M. Helmchen G., Hoffmann R.W., Mulzer J., Schaumann E., Houben-Weyl: Methods of Organic Chemistry. Vol. E 21:1995;1730 Georg Thieme Verlag, Stuttgart, (d) Nelson S.G. Tetrahedron: Asymmetry. 9:1998;357 (e) Gröger H., Vogl E.M., Shibasaki M. Chem. Eur. J. 4:1998;1137 (f) Mahrwald R. Chem. Rev. 99:1999;1095 (g) Carreira E.M. Jacobsen E.N., Pfaltz A., Yamamoto H., Comprehensive Asymmetric Catalysis. Vol. 3:1999;997 Springer, Heidelberg, (h) Arya P., Qin H. Tetrahedron. 56:2000;917 (i) Machajewski T.D., Wong C.-H. Angew. Chem. Int. Ed. 39:2000;1352 (j) Carreira E.M. Otera J., Modern Carbonyl Chemistry. 2000;227 Wiley-VCH, Weinheim. Chapter 8 (k) Yamamoto H., Lewis Acids in Organic Synthesis. Vols. 1 and 2:2000;Wiley-VCH, Weinheim.
    • (2000) Lewis Acids in Organic Synthesis , vol.1-2
    • Yamamoto, H.1
  • 46
  • 47
    • 0033935920 scopus 로고    scopus 로고
    • Reviews for chiral Lewis base-catalyzed asymmetric aldol reactions using trichlorosilyl enol ethers: (a) Denmark S.E., Stavenger R.A., Su X., Wong K.-T., Nishigaichi Y. Pure Appl. Chem. 70:1998;1469 (b) Denmark S.E., Stavenger R.A. Acc. Chem. Res. 33:2000;432.
    • (2000) Acc. Chem. Res. , vol.33 , pp. 432
    • Denmark, S.E.1    Stavenger, R.A.2
  • 48
    • 0035793248 scopus 로고    scopus 로고
    • Reviews for direct catalytic asymmetric aldol reactions of aldehydes with unmodified ketones: (a) Gröger H., Wilken J. Angew. Chem. Int. Ed. 40:2001;529 (b) List B. Synlett. 2001;1675.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 529
    • Gröger, H.1    Wilken, J.2
  • 49
    • 0034750244 scopus 로고    scopus 로고
    • Reviews for direct catalytic asymmetric aldol reactions of aldehydes with unmodified ketones: (a) Gröger H., Wilken J. Angew. Chem. Int. Ed. 40:2001;529 (b) List B. Synlett. 2001;1675.
    • (2001) Synlett , pp. 1675
    • List, B.1
  • 67
    • 0000548610 scopus 로고
    • For spectral data of the racemic compound, see: (a) Huckin S.N., Weiler L. Can. J. Chem. 52:1974;2157 (b) Takahashi K., Kishi M. Tetrahedron. 44:1988;4737.
    • (1974) Can. J. Chem. , vol.52 , pp. 2157
    • Huckin, S.N.1    Weiler, L.2
  • 68
    • 0023747590 scopus 로고
    • For spectral data of the racemic compound, see: (a) Huckin S.N., Weiler L. Can. J. Chem. 52:1974;2157 (b) Takahashi K., Kishi M. Tetrahedron. 44:1988;4737.
    • (1988) Tetrahedron , vol.44 , pp. 4737
    • Takahashi, K.1    Kishi, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.