메뉴 건너뛰기




Volumn 59, Issue 40, 2003, Pages 7973-7981

Asymmetric dihydroxylation of vinyl sulfones: Routes to enantioenriched α-hydroxyaldehydes and the enantioselective syntheses of furan-2(5H)-ones

Author keywords

Asymmetric dihydroxylation; Prochiral alkene; Vinyl sulfones; hydroxyaldehydes

Indexed keywords

8 (OXO 2,5 DIHYDROFURAN 2 YL)OCTANOIC ACID ETHYL ESTER; ALDEHYDE DERIVATIVE; BUTYLMETHYLDIHYDROFURAN 2 ONE; FURANONE DERIVATIVE; KETONE DERIVATIVE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

EID: 0141628814     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.08.003     Document Type: Article
Times cited : (57)

References (50)
  • 2
    • 0028058771 scopus 로고
    • For one of many examples of dihydroxylation with an α,β -unsaturated carbonyl compounds see:
    • For one of many examples of dihydroxylation with an α,β -unsaturated carbonyl compounds see: Wang Z.-M., Kolb H.C., Sharpless K.B. J. Org. Chem. 59:1994;5104.
    • (1994) J. Org. Chem. , vol.59 , pp. 5104
    • Wang, Z.-M.1    Kolb, H.C.2    Sharpless, K.B.3
  • 3
    • 0003620128 scopus 로고
    • Pergamon, Oxford
    • (a) Simpkins N.S. Sulphones in Organic Chemistry. 1993;Pergamon, Oxford, (b) Simpkins N.S. Tetrahedron. 46:1990;6951 (c) Fuchs P.L., Braish T.F. Chem. Rev. 86:1986;903.
    • (1993) Sulphones in Organic Chemistry
    • Simpkins, N.S.1
  • 4
    • 0000036801 scopus 로고
    • (a) Simpkins N.S. Sulphones in Organic Chemistry. 1993;Pergamon, Oxford, (b) Simpkins N.S. Tetrahedron. 46:1990;6951 (c) Fuchs P.L., Braish T.F. Chem. Rev. 86:1986;903.
    • (1990) Tetrahedron , vol.46 , pp. 6951
    • Simpkins, N.S.1
  • 5
    • 33845374037 scopus 로고
    • (a) Simpkins N.S. Sulphones in Organic Chemistry. 1993;Pergamon, Oxford, (b) Simpkins N.S. Tetrahedron. 46:1990;6951 (c) Fuchs P.L., Braish T.F. Chem. Rev. 86:1986;903.
    • (1986) Chem. Rev. , vol.86 , pp. 903
    • Fuchs, P.L.1    Braish, T.F.2
  • 6
    • 0000288426 scopus 로고
    • For representative synthetic applications of α-hydroxy aldehydes see: (a) Kobori Y., Myles D.C., Whitesides G.M. J. Org. Chem. 57:1992;5899 (b) Petasis N., Zavialov I.A. J. Am. Chem. Soc. 120:1998;11798 (c) Ko K.-Y., Frazee W.J., Eliel E.L. Tetrahedron. 40:1984;1333 (d) Humphrey A.J., Turner N.J., McCague R., Taylor S.J.C. J. Chem. Soc., Chem. Commun. 1995;2475. and references therein.
    • (1992) J. Org. Chem. , vol.57 , pp. 5899
    • Kobori, Y.1    Myles, D.C.2    Whitesides, G.M.3
  • 7
    • 0032544945 scopus 로고    scopus 로고
    • For representative synthetic applications of α-hydroxy aldehydes see: (a) Kobori Y., Myles D.C., Whitesides G.M. J. Org. Chem. 57:1992;5899 (b) Petasis N., Zavialov I.A. J. Am. Chem. Soc. 120:1998;11798 (c) Ko K.-Y., Frazee W.J., Eliel E.L. Tetrahedron. 40:1984;1333 (d) Humphrey A.J., Turner N.J., McCague R., Taylor S.J.C. J. Chem. Soc., Chem. Commun. 1995;2475. and references therein.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 11798
    • Petasis, N.1    Zavialov, I.A.2
  • 8
    • 0001127065 scopus 로고
    • For representative synthetic applications of α-hydroxy aldehydes see: (a) Kobori Y., Myles D.C., Whitesides G.M. J. Org. Chem. 57:1992;5899 (b) Petasis N., Zavialov I.A. J. Am. Chem. Soc. 120:1998;11798 (c) Ko K.-Y., Frazee W.J., Eliel E.L. Tetrahedron. 40:1984;1333 (d) Humphrey A.J., Turner N.J., McCague R., Taylor S.J.C. J. Chem. Soc., Chem. Commun. 1995;2475. and references therein.
    • (1984) Tetrahedron , vol.40 , pp. 1333
    • Ko, K.-Y.1    Frazee, W.J.2    Eliel, E.L.3
  • 9
    • 37049072050 scopus 로고
    • For representative synthetic applications of α-hydroxy aldehydes see: (a) Kobori Y., Myles D.C., Whitesides G.M. J. Org. Chem. 57:1992;5899 (b) Petasis N., Zavialov I.A. J. Am. Chem. Soc. 120:1998;11798 (c) Ko K.-Y., Frazee W.J., Eliel E.L. Tetrahedron. 40:1984;1333 (d) Humphrey A.J., Turner N.J., McCague R., Taylor S.J.C. J. Chem. Soc., Chem. Commun. 1995;2475. and references therein.
    • (1995) J. Chem. Soc., Chem. Commun. , pp. 2475
    • Humphrey, A.J.1    Turner, N.J.2    McCague, R.3    Taylor, S.J.C.4
  • 10
    • 0032554983 scopus 로고    scopus 로고
    • To the best of our knowledge this type of transformation has been reported previously on two occasions in the diastreoselective dihydroxylation of trisubstituted vinyl sulfones: (a) Fiegelson G.B. Tetrahedron Lett. 39:1998;3387 (b) Löfström C.M.G., Ericsson A.M., Bourrinet L., Juntunen S.K., Bäckvall J.-E. J. Org. Chem. 60:1995;3586.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 3387
    • Fiegelson, G.B.1
  • 11
    • 0000408659 scopus 로고
    • To the best of our knowledge this type of transformation has been reported previously on two occasions in the diastreoselective dihydroxylation of trisubstituted vinyl sulfones: (a) Fiegelson G.B. Tetrahedron Lett. 39:1998;3387 (b) Löfström C.M.G., Ericsson A.M., Bourrinet L., Juntunen S.K., Bäckvall J.-E. J. Org. Chem. 60:1995;3586.
    • (1995) J. Org. Chem. , vol.60 , pp. 3586
    • Löfström, C.M.G.1    Ericsson, A.M.2    Bourrinet, L.3    Juntunen, S.K.4    Bäckvall, J.-E.5
  • 12
    • 0032796561 scopus 로고    scopus 로고
    • (a) Marquis C., Picasso S., Vogel P. Synthesis. 1999;1441 (b) Schaller C., Vogel P. Helv. Chim. Acta. 83:2000;193 (c) Trost B.M., Pinkerton A.B. J. Am. Chem. Soc. 124:2002;7376.
    • (1999) Synthesis , pp. 1441
    • Marquis, C.1    Picasso, S.2    Vogel, P.3
  • 13
    • 0033951889 scopus 로고    scopus 로고
    • (a) Marquis C., Picasso S., Vogel P. Synthesis. 1999;1441 (b) Schaller C., Vogel P. Helv. Chim. Acta. 83:2000;193 (c) Trost B.M., Pinkerton A.B. J. Am. Chem. Soc. 124:2002;7376.
    • (2000) Helv. Chim. Acta , vol.83 , pp. 193
    • Schaller, C.1    Vogel, P.2
  • 14
    • 0037178098 scopus 로고    scopus 로고
    • (a) Marquis C., Picasso S., Vogel P. Synthesis. 1999;1441 (b) Schaller C., Vogel P. Helv. Chim. Acta. 83:2000;193 (c) Trost B.M., Pinkerton A.B. J. Am. Chem. Soc. 124:2002;7376.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 7376
    • Trost, B.M.1    Pinkerton, A.B.2
  • 16
    • 0022626633 scopus 로고
    • (a) Mizutani T., Honzawa S., Tosaki S., Shibasaki M. Angew. Chem., Int. Ed. Engl. 41:2002;4680 (b) Dyong I., Meyer W., Thiem J. Liebigs Ann. 1986;613.
    • (1986) Liebigs Ann. , pp. 613
    • Dyong, I.1    Meyer, W.2    Thiem, J.3
  • 19
    • 0033615596 scopus 로고    scopus 로고
    • (a) Dupau P., Epple R., Thomas A.A., Fokin V.V., Sharpless K.B. Adv. Synth. Catal. 2002;421 (b) Thomas A.A., Sharpless K.B. J. Org. Chem. 64:1999;8379.
    • (1999) J. Org. Chem. , vol.64 , pp. 8379
    • Thomas, A.A.1    Sharpless, K.B.2
  • 20
    • 0036007699 scopus 로고    scopus 로고
    • and references therein
    • (a) For a general review see: Chemla, F. J. Chem. Soc., Perkin Trans. 1 2002, 275 and references therein. (b) Hwu J.R. J. Org. Chem. 48:1983;4432 (c) Little R.D., Myong S.O. Tetrahedron Lett. 21:1980;3339. (d) for examples of this method in target synthesis see: Caldwell J.J., Craig D., East S.P. Synlett. 2001;1602 (e) Paquette L.A., Barriault L., Pissarnitski D., Johnson J.N. J. Am. Chem. Soc. 122:2000;619.
    • (2002) J. Chem. Soc., Perkin Trans. 1 , pp. 275
    • Chemla, F.1
  • 21
    • 0000109040 scopus 로고
    • (a) For a general review see: Chemla, F. J. Chem. Soc., Perkin Trans. 1 2002, 275 and references therein. (b) Hwu J.R. J. Org. Chem. 48:1983;4432 (c) Little R.D., Myong S.O. Tetrahedron Lett. 21:1980;3339. (d) for examples of this method in target synthesis see: Caldwell J.J., Craig D., East S.P. Synlett. 2001;1602 (e) Paquette L.A., Barriault L., Pissarnitski D., Johnson J.N. J. Am. Chem. Soc. 122:2000;619.
    • (1983) J. Org. Chem. , vol.48 , pp. 4432
    • Hwu, J.R.1
  • 22
    • 0000130998 scopus 로고
    • (a) For a general review see: Chemla, F. J. Chem. Soc., Perkin Trans. 1 2002, 275 and references therein. (b) Hwu J.R. J. Org. Chem. 48:1983;4432 (c) Little R.D., Myong S.O. Tetrahedron Lett. 21:1980;3339. (d) for examples of this method in target synthesis see: Caldwell J.J., Craig D., East S.P. Synlett. 2001;1602 (e) Paquette L.A., Barriault L., Pissarnitski D., Johnson J.N. J. Am. Chem. Soc. 122:2000;619.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 3339
    • Little, R.D.1    Myong, S.O.2
  • 23
    • 0034805394 scopus 로고    scopus 로고
    • (a) For a general review see: Chemla, F. J. Chem. Soc., Perkin Trans. 1 2002, 275 and references therein. (b) Hwu J.R. J. Org. Chem. 48:1983;4432 (c) Little R.D., Myong S.O. Tetrahedron Lett. 21:1980;3339. (d) for examples of this method in target synthesis see: Caldwell J.J., Craig D., East S.P. Synlett. 2001;1602 (e) Paquette L.A., Barriault L., Pissarnitski D., Johnson J.N. J. Am. Chem. Soc. 122:2000;619.
    • (2001) Synlett , pp. 1602
    • Caldwell, J.J.1    Craig, D.2    East, S.P.3
  • 24
    • 0033980986 scopus 로고    scopus 로고
    • (a) For a general review see: Chemla, F. J. Chem. Soc., Perkin Trans. 1 2002, 275 and references therein. (b) Hwu J.R. J. Org. Chem. 48:1983;4432 (c) Little R.D., Myong S.O. Tetrahedron Lett. 21:1980;3339. (d) for examples of this method in target synthesis see: Caldwell J.J., Craig D., East S.P. Synlett. 2001;1602 (e) Paquette L.A., Barriault L., Pissarnitski D., Johnson J.N. J. Am. Chem. Soc. 122:2000;619.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 619
    • Paquette, L.A.1    Barriault, L.2    Pissarnitski, D.3    Johnson, J.N.4
  • 28
    • 0035801862 scopus 로고    scopus 로고
    • (a) Grela K., Bieniek M. Tetrahedron Lett. 42:2001;6425 (b) Michrowska A., Bieniek M., Kim M., Klajn R., Grela K. Tetrahedron. 59:2003;4525.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 6425
    • Grela, K.1    Bieniek, M.2
  • 32
    • 0000848467 scopus 로고
    • For a similar example using the Still-Gennari method for the synthesis of furan-2(5H)-ones see:
    • For a similar example using the Still-Gennari method for the synthesis of furan-2(5H)-ones see: Beckmann M., Hilderbrandt H., Winterfeldt E. Tetrahedron: Asymmetry. 1:1990;335.
    • (1990) Tetrahedron: Asymmetry , vol.1 , pp. 335
    • Beckmann, M.1    Hilderbrandt, H.2    Winterfeldt, E.3
  • 34
    • 0024451049 scopus 로고
    • and references therein
    • (a) Carter N.B., Nadany A.E., Sweeney J.B. J. Chem. Soc., Perkin Trans. 1. 2002;2324 (b) Nagao Y., Bai W.-M., Ochiai M., Shiro M. J. Org. Chem. 54:1989;5211. and references therein.
    • (1989) J. Org. Chem. , vol.54 , pp. 5211
    • Nagao, Y.1    Bai, W.-M.2    Ochiai, M.3    Shiro, M.4
  • 35
    • 0029592717 scopus 로고
    • (a) Hoppe R., Scharf H.-D. Synthesis. 1995;1447 (b) He Y.-T., Yang H.-N., Yao Z.-J. Tetrahedron. 58:2002;8805.
    • (1995) Synthesis , pp. 1447
    • Hoppe, R.1    Scharf, H.-D.2
  • 38
    • 0029939024 scopus 로고    scopus 로고
    • (a) Kern W., Spiteller G. Tetrahedron. 52:1996;4347. and references therein (b) Siedlecka R., Skarzewski J., Mlochowski J. Tetrahedron Lett. 31:1990;2177 (c) Ogura K., Tsuchihashi G. Tetrahedron Lett. 26:1972;2681.
    • (1996) Tetrahedron , vol.52 , pp. 4347
    • Kern, W.1    Spiteller, G.2
  • 39
    • 0025219293 scopus 로고
    • (a) Kern W., Spiteller G. Tetrahedron. 52:1996;4347. and references therein (b) Siedlecka R., Skarzewski J., Mlochowski J. Tetrahedron Lett. 31:1990;2177 (c) Ogura K., Tsuchihashi G. Tetrahedron Lett. 26:1972;2681.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 2177
    • Siedlecka, R.1    Skarzewski, J.2    Mlochowski, J.3
  • 40
    • 0002348725 scopus 로고
    • and references therein
    • (a) Kern W., Spiteller G. Tetrahedron. 52:1996;4347. and references therein (b) Siedlecka R., Skarzewski J., Mlochowski J. Tetrahedron Lett. 31:1990;2177 (c) Ogura K., Tsuchihashi G. Tetrahedron Lett. 26:1972;2681.
    • (1972) Tetrahedron Lett. , vol.26 , pp. 2681
    • Ogura, K.1    Tsuchihashi, G.2
  • 41
    • 84985269054 scopus 로고
    • (a) Günther C., Mosandl A. Liebigs Ann. Chem. 1986;2112 (b) Bloch R., Gilbert L. J. Org. Chem. 52:1987;4603 (c) Suzuki K., Shoji M., Kobayashi E., Inomata K. Tetrahedron: Asymmetry. 12:2001;2789.
    • (1986) Liebigs Ann. Chem. , pp. 2112
    • Günther, C.1    Mosandl, A.2
  • 42
    • 0001001461 scopus 로고
    • (a) Günther C., Mosandl A. Liebigs Ann. Chem. 1986;2112 (b) Bloch R., Gilbert L. J. Org. Chem. 52:1987;4603 (c) Suzuki K., Shoji M., Kobayashi E., Inomata K. Tetrahedron: Asymmetry. 12:2001;2789.
    • (1987) J. Org. Chem. , vol.52 , pp. 4603
    • Bloch, R.1    Gilbert, L.2
  • 45
    • 0032415724 scopus 로고    scopus 로고
    • 4 mg of maritolide 20 was isolated from 16 kg of diospyros maritima stems
    • Kuo Y.-H., Huang S.L., Chang C.-I. Phytochemistry. 49:1998;2505. [4 mg of maritolide 20 was isolated from 16 kg of diospyros maritima stems].
    • (1998) Phytochemistry , vol.49 , pp. 2505
    • Kuo, Y.-H.1    Huang, S.L.2    Chang, C.-I.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.