One-pot synthesis of (3R)-hydroxy-β-lactams via enolates of 2-tert-butyl-1,3-dioxolan-4-ones. Part 1

Tetrahedron Asymmetry

Volumn 8, Issue 15, 1997, Pages 2527-2531

  Barbaro, Gaetano ^a   Battaglia, Arturo ^a   Guerrini, Andrea ^a   Bertucci, Carlo ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0030790661     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00303-0     Document Type: Article

References (21)

1. Miller, M. J. Acc. Chem. Res. 1986, 19, 49-56
2. For a leading reference dealing with the "SRS" principle see: Seebach, D.; Sting A. R.; Hoffmann. M. Angew. Chem. Int. Ed. Engl. 1996, 35, 2708-2748. According to this principle a substituent at a stereogenic center of a chiral molecule is replaced without racemization and without the use of a chiral auxiliary. This has been accomplished in a four step sequence, i.e.: (a) a temporary stereogenic center is generated diastereoselectively, (b) the original stereogenic center is trigonalized by removal of a substituent, (c) a new ligand is introduced diastereoselectively, (d) the temporary center is finally removed.
3. Seebach, D.; Hungerbuhler E. Modern Synthetic Methods, Scheffold R. Ed., 1980, Vol. 2, pp. 91-171, Salle+Sauerlander, Aarau, Switzerland.
4. (a) Seebach, D.; Naef, R.; Calderari, G. Tetrahedron 1984, 40, 1313-1324.
5. (b) Chapel, N.; Greiner, A.; Ortholand, J. Y. Tetrahedron Lett. 1991, 40, 1441-1442.
6. There is some confusion when the term cis/trans is used to define the relative configuration of 3-hydroxy-β-lactams which bear a quaternary stereogenic center at C3. For instance, according to Newcomb the β-lactams (3R,4S)-Z-4a,b are cis-isomers, instead, according to Palomo are transisomers. To avoid this confusion, we have used, according to the nomenclature used by Bose, the terms Z/E instead of cis/trans. See: (a) Gluchowski, C.; Cooper, L.; E. Bergbreiter, D. E.; Newcomb, M. J. Org. Chem. 1980, 45, 3413-3416.
7. (b) Palomo, C.; Cossio, F. P.; Odiozola, J. M.; Oiarbide, M.; Ontoria, J. M. J. Org. Chem. 1991, 56, 4418-4428.
8. (c) Bose, A. K.; Lal, B.; Dayal, B.; Manhas, M. S. Tertrahedron Lett. 1974, 30, 2633-2636.
9. HPLC: Column Chiralpack AD (Daicel 250×4.0 mm). The mobile phase was n-hexane/2-propanol (90:10, 80:20, 50:50, v/v), 0.8 or 1.0 mL/min flow. The chromatographic retentions of the solutes were followed by a JASCO multi-340 multi channel detector. The eluates were also monitored by using a JASCO J 710 spectro-polarimeter (set at 250 nm) equipped with a micro HPLC cell. This detection system allows the absorption and the circular dichroism (CD) signals to be simultaneously detected. CD measurements were carried out by a J600 spectropolarimeter (c=0.4 mM, EtOH).
10. Robbins, M. J.; Wilson, J. S.; Hansske, F. J. Am. Chem. Soc. 1983, 105, 4059-4065.
11. (a) Kagan, H. B.; Basselier, J. J.; Luche, J. L. Tetrahedron Lett. 1964, 941-948.
12. (b) Ha, D. C.; Hart, D. J.; Yang, T. K. J. Amer. Chem. Soc, 1984, 106, 4819-4825.
13. As expected on the basis of the literature data, the circular dichroism spectrum of β-lactam (3S,4S)-Z-10 was negative at 240 nm. See: Galle, D.; Tolksdorf, M.; Braun, M. Tetrahedron Lett. 1995, 36, 4217-4220. This result allowed the assignment of absolute configuration of (3R,4R)-E-4a. 10. Also the thermal decompostion of the lithium enolate of the (2S,5S)-2-(tert-butyl)-5-isopropyl-1,3-dioxolan-4-one afforded the corresponding 2-hydroxy-2,N,N-trimethylbutyramide. See: Ogawa, T.; Niwa, H.; Yamada, K. Tetrahedron 1993, 49, 1571-1578.
14. As expected on the basis of the literature data, the circular dichroism spectrum of β-lactam (3S,4S)-Z-10 was negative at 240 nm. See: Galle, D.; Tolksdorf, M.; Braun, M. Tetrahedron Lett. 1995, 36, 4217-4220. This result allowed the assignment of absolute configuration of (3R,4R)-E-4a. 10. Also the thermal decompostion of the lithium enolate of the (2S,5S)-2-(tert-butyl)-5-isopropyl-1,3-dioxolan-4-one afforded the corresponding 2-hydroxy-2,N,N-trimethylbutyramide. See: Ogawa, T.; Niwa, H.; Yamada, K. Tetrahedron 1993, 49, 1571-1578.
15. LHMDS is also recommended in the alky lation of a number of dioxolanones, to avoid the addition of pivalaldehyde to the corresponding enolates.
16. An identical result was obtained when 1,3-dimethyl-3,4,5,6-tetrahydro-2-(1H)-pyrimidone (DMPU), instead of HMPA, was used.
17. (a) Cossio, F. P.; Palomo, C. Tertrahedron Lett. 1985, 55, 4239-4242.
18. (b) Bose, A. K.; Dayal, B.; Manhas, M. S; Kapur, J. C.; Lal, B. Tertrahedron Lett. 1974, 36, 3135-3138.
19. 5a
20. It is worth noting that both enantiomers are available if either one of the enantiomeric starting α-hydroxyacids or if either one of the cis-or the trans-dioxolanones are available.
21. 15NO: C, 80.98; H, 6.37; N, 5.90. Found: C, 81.10; H, 6.40; N, 5.82.