Stereoselective synthesis of 3-(ω-hydroxyalkyl)-2-pyrrolidinones from α-alkylidenelactones and nitromethane

Tetrahedron Asymmetry

Volumn 10, Issue 17, 1999, Pages 3381-3389

  Otto, Andreas ^a   Abegaz, Berhanu ^b   Ziemer, Burkhard ^a   Liebscher, Jürgen ^a  

^a HUMBOLDT UNIVERSITY   (Germany)

^b UNIVERSITY OF BOTSWANA   (Botswana)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDINONE; 2 PYRROLIDONE DERIVATIVE; ALKYL GROUP; LACTONE DERIVATIVE; NITROMETHANE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; CRYSTAL STRUCTURE; CYCLIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033431864     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00346-8     Document Type: Article

References (11)

1. Otto, A.; Ziemer, B.; Liebscher J. Synthesis 1999, 965.
2. Houk, K. N.; Paddon-Row, M. N.; Rondan, N. G.; Wu, Y. D.; Brown, F. K.; Spellmeyer, D. C.; Metz, J. T.; Li, Y.; Loncharich, R. J. Science 1986, 231, 1108.
3. Caramella, P. N.; Rondan, G.; Paddon-Row, M. N.; Houk, K. N. J. Am. Chem. Soc. 1981, 103, 2438.
4. Mulzer, J.; Altenbach, H. J.; Braun, M.; Krohn, K.; Reissig, H. U. Organic Synthesis Highlights; VCH: Weinheim, 1991; 4 and 247.
5. Fuji, K.; Zheng, S.-Z.; Node, M.; Hao X.-J. Chem. Pharm. Bull. 1991, 39, 202.
6. Hao, X.-J.; Node, M.; Fuji, K. J. Chem. Soc., Perkin Trans. 1 1992, 1505.
7. Schmidt, M.; Eger, K. Pharmazie 1996, 51, 11.
8. Nishide, K.; Katoh, T.; Imazato, H.; Node, M. Heterocycles 1998, 47, 839.
9. Takano, S.; Sato, T.; Inomata, K.; Ogasawara, K. Heterocycles 1990, 31, 411.
10. Otto, A.; Ziemer, B.; Liebscher, J. Eur. J. Org. Chem. 1998, 2667; erroneous configurations were given for compounds 7c, 11a, 11g in this paper. The correct configurations are for 7c:1′R,E; for 11a: 4S, 5R, 4′S; and for 11g: 4R, 5S, 1′R.
11. Crystallographic data for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-133192 (2b), CCDC-133190 (9d), CCDC-133191 (12). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: 44-1223/336-033; e-mail: deposit@ccdc.cam.ac.uk).