Enantioselective syntheses of orthogonally protected tricarballylic acid esters

Tetrahedron Letters

Volumn 41, Issue 8, 2000, Pages 1261-1264

  Harmat, Nicholas J S ^a   Mangani, Silvia ^a   Perrotta, Enzo ^a   Giannotti, Danilo ^a   Nannicini, Rossano ^a   Altamura, Maria ^a  

^a Menarini Ricerche SpA   (Italy)

Author keywords

Alkylation; Asymmetric synthesis; Carboxylic acids; Oxazolidinones; Protecting groups

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; GLUTARIC ACID DERIVATIVE; OXAZOLIDINONE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; ESTERIFICATION; HYDROLYSIS; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034685247     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02264-9     Document Type: Article

References (14)

1. (a) Christy, M. R.; Barkley, M. R.; Koch, T. H.; Van Buskirk, J. J.; Kirsc, W. M. J. Am. Chem. Soc. 1981, 103, 3935-3937;
2. (b) Shier, W. T.; Habbes, H. K.; Badria, F. A. Tetrahedron Lett. 1995, 36, 1571-1574;
3. (c) Aoyama; T.; Sato, T.; Yonemoto, M.; Shibata, J.; Nanoshita, K.; Arai, S.; Kawakami, K.; Iwasawa, Y.; Sano, H.; Tanaka, K.; Monden, Y.; Kodera, T.; Arakawa, H.; Suzuki-Takahashi, I.; Kamei, T.; Tomimoto, K. J. Med. Chem. 1998, 41, 143-147.
4. (a) Boyle, C. D.; Kishi, Y. Tetrahedron Lett. 1995, 36, 4579-4582;
5. (b) Edwards, O. E.; Blackwell, A. B.; Driega, B. A.; Bensimon C.; Apsimon, J. W. Tetrahedron Lett. 1999, 40, 763-795.
6. Perrotta, E.; Harmat, N. J. S.; Mangani, S.; Raffaelli, B.; Giannotti, D.; Nannicini R.; Altamura, M.; Poster n.138, ESOC 11, Goteborg, Sweden, 1999.
7. Hanessian, S.; Gomtsyan, A.; Payne, A.; Hervè, Y.; Beaudoin, S. J. Org. Chem. 1993, 58, 5032-5034.
8. Arvanitis, E.; Motevalli, M.; Wyatt, P. B. Tetrahedron Lett. 1996, 37, 4277-4280.
9. Perrotta, E.; Raffaelli, B.; Giannotti, D.; Harmat, N. J. S.; Nannicini, R.; Altamura, M. Synlett 1999, 144-146.
10. Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411-6417.
11. Carlsen, P. H. J.; Tatsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936-3938.
12. 6: C, 63.34; H, 6.88. Found: C, 63.23; H, 6.89.
13. Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127-2129.
14. 5: C, 65.31; H, 7.79; N, 4.01. Found: C, 65.25; H, 7.81; N, 3.97.