Highly diastereoselective hetero-Diels-Alder reaction of buta-1,3-diene with N-glyoxyloyl-(2R)-bornane-10,2-sultam: An efficient synthesis of homochiral (S)-3-[2-{(methylsulfonyl)oxy}ethoxy]-4-(triphenylmethoxy)-1-butanol methanesulfonate

Tetrahedron Asymmetry

Volumn 14, Issue 2, 2003, Pages 239-244

  Kosior, Małgorzata ^a   Malinowska, Małgorzata ^a   Jóźwik, Julita ^a   Caille, Jean Claude ^b   Jurczak, Janusz ^a,c  

^a UNIVERSITY OF WARSAW   (Poland)

^b PPG SIPSY   (France)

^c INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE; 3 [2 [(METHYLSULFONYL)OXY]ETHOXY] 4 (TRIPHENYLMETHOXY) 1 BUTANOL METHANESULFONATE; BORNANE DERIVATIVE; LEWIS ACID; MESYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG; ZINC BROMIDE;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CATALYST; CHIRALITY; CRYSTAL STRUCTURE; CYCLOADDITION; DIASTEREOISOMER; DIELS ALDER REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0037449671     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00746-2     Document Type: Article

References (14)

1. Tamaoki T., Namoto H., Takahashi I., Kato Y., Morimoto M., Tomita F. Biochem. Biophys. Res. Commun. 135:1986;397.
2. Bush J.A., Long B.H., Catino J.J., Brandner W.T., Tomita K. J. Antibiot. 40:1987;668.
3. Inoguchi T., Battan R., Handler E., Sportsman J.R., Heath W., King G.L. Proc. Natl. Acad. Sci. USA. 89:1992;11059.
4. Jirousek M.R., Gilling J.R., Gonzalez C.M., Heath W., McDonald J.H. III, Neel D.A., Rito Ch.J., Singh U., Stramm L.E., Melikian-Badalian A., Baevsky M., Ballas L.M., Hall S.E., Faul M.M., Winneroski L. J. Med. Chem. 39:1996;2664.
5. Faul M.M., Winneroski L.L., Krumrich Ch.A., Sullivan K.A., Gilling J.R., Neel D.A., Rito Ch.J., Jirousek M.R. J. Org. Chem. 63:1998;1961-1973.
6. Caille, J.-C.; Govindan, C. K.; Junga, H.; Lalonde, J.; Yao, Y., to be published.
7. Bauer T., Jezewski A., Chapuis C., Jurczak J. Tetrahedron: Asymmetry. 7:1996;1385.
8. Oppolzer W., Chapuis C., Bernardinelli G. Helv. Chim. Acta. 67:1984;1397.
9. Kosior, M.; Malinowska, M.; Jurczak, J. unpublished results.
10. Jurczak J., Tkacz M. J. Org. Chem. 44:1979;3347.
11. Jurczak J., Chmielewski M., Filipek S. Synthesis. 1979;41.
12. Sheldrick G.M. Acta Crystallogr. A46:1990;467-473.
13. Sheldrick, G. M. SHELXL-93. Program for the Refinement of Crystal Structures, University of Göttingen, Germany.
14. International Tables for Crystallography; Wilson, A. J. C., Ed.; Kluwer: Dordrecht, 1992; Vol. C.