Alkylation of 4-hydroxyproline ester derivatives. Diastereoselectivity guided by the anomeric effect and π-interaction

Tetrahedron Letters

Volumn 40, Issue 16, 1999, Pages 3209-3212

  Nagumo, Shinji ^a   Mizukami, Megumi ^a   Akutsu, Noriaki ^a   Nishida, Atsushi ^a,b   Kawahara, Norio ^a  

^a HOKKAIDO INSTITUTE OF TECHNOLOGY   (Japan)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATING AGENT; AMINO ACID DERIVATIVE; HYDROXYPROLINE;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; MOLECULAR INTERACTION; MOLECULAR MODEL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033574562     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00468-2     Document Type: Article

References (12)

1. (a) Seebach, D.; Juaristi, E.; Miller, D. D.; Schickli, C.; Weber, T. Helv. Chim. Acta 1987, 70, 237.
2. (b) Seebach, D.; Maetzke, T.; Petter, W.; Klotzer, B.; Plattner, D. A. J. Am. Chem. Soc. 1991, 113, 1781.
3. Hon, Y.-S.; Chang, Y.-C; Gong, M.-L. Heterocycles 1990, 31, 191.
4. Meyers, A. I.; Seefeld, M. A.; Lefker, B. A.; Blake, J. F. J. Am. Chem. Soc. 1997, 119, 4565.
5. Seebach, D.; Aebi, J. D.; Gander-Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194.
6. Shiosaki, K.; Rapoport, H. J. Org. Chem. 1985, 50, 1229.
7. Shioiri, T.; Ninomiya, K.; Yamada, S. J. Am. Chem. Soc. 1972, 94, 6203.
8. A similar concept was mentioned by McIntosh et al., to explain the highly stereoselective alkylation of the (R)-camphor imine of glycinate with benzylic halides. (a) McIntosh, J. M.; Mishra, P. Can. J. Chem. 1986, 64, 726.
9. (b) McIntosh, J. M.; Leavitt, R. K.; Mishra, P.; Cassidy, K. C.; Darke, J. E.; Chadha, R. J. Org. Chem. 1988, 53, 1947.
10. For alkylation of 4-hydroxyproline monocyclic enolate: (a) Sato, T.; Kugo, Y.; Nakaumi, E.; Ishibashi, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1995, 1801.
11. (b) Noe, C. R.; Knollmueller, M.; Voellenkle, H.; Noe-Letsching, M.; Weigand, A.; Muehl, J. Pharmazie 1996, 51, 800.
12. Seebach reported that the corresponding bicyclic enolate proceeded in a highly stereoselective manner. However, the yield was very low. Weber, T.; Seebach, D. Helv. Chim. Acta 1985, 68, 155.