Tricarbonyl(η6-arene)chromium(0) complexes as chiral auxiliaries: Asymmetric synthesis of β-lactones

Molecules

Volumn 6, Issue 1, 2001, Pages 13-20

  Del Buttero, Paola ^a   Montrasio, Deborah ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

2 oxetanones; Chromiumtricarbonyl benzaldehydes; Stereoselective synthesis; lactones

Indexed keywords

CHROMIUM DERIVATIVE; HYDROXYACID; LACTONE DERIVATIVE; TRICARBONYL(ETA6 ARENE)CHROMIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHIRALITY; COMPLEX FORMATION; POLYMERIZATION; QUANTUM YIELD; RING CLOSING METATHESIS;

EID: 3242763002     PISSN: 14203049     EISSN: None     Source Type: Journal    
DOI: 10.3390/60100013     Document Type: Article

References (20)

1. Pommier, A.; Pons, J. M. The synthesis of natural 2-oxetanones. Synthesis 1995, 729-744.
2. Pommier, A.; Pons, J.M. Recent advances in β-lactone chemistry. Synthesis 1993, 441-459.
3. Abe, H.; Matsubara, I.; Doi, Y. Physical properties and enzymatic degradability of polymer blends of bacterial poly[(R)-3-hydroxybutyrate] and poly[(R,S)-3-hydroxybutyrate] stereoisomers. Macromolecules 1995, 28, 844-853.
4. 6-arene)chromium(0) complexes as chiral auxiliaries. Homochiral β-lactams synthesis "via" [2+2] cycloaddition reaction. Tetrahedron: Asymmetry 1994, 5, 809-812.
5. 6-arene)chromium(0) complexes as chiral auxiliaries. Asymmetric Synthesis of β-aminoesters and β-lactams by Reformatsky condensation. Tetrahedron 1996, 52, 4849-4856.
6. 6-arene) chromium(0) complexes. Tetrahedron 1999, 55, 14089-14096.
7. 6-arene)chromium(0) complex. Tetrahedron: Asymmetry 2000, 11, 1927-1941.
8. Yang, H. W.; Romo, D. Methods for the synthesis of optically active β-lactones (2-oxetanones). Tetrahedron 1999, 55, 6403-6434.
9. Case-Green, S. C.; Davies, S. G.; Hedgecock, C. J. R. Asymmetric Synthesis of Homochiral β-lactones via the Iron Chiral Auxiliary. Synlett 1991, 779-780.
10. Case-Green, S. C.; Davies, S. G.; Hedgecock, C. J. R. Asymmetric Synthesis of (-)-Tetrahydrolipstatin. Synlett 1991, 781-782.
11. Petragnani, N.; Yonashiro, M. The reactions of dianion of carboxylic acids and ester enolates. Synthesis 1982, 521-578.
12. Del Buttero, P.; Baldoli, C. Arenechromiumtricarbonyl derivatives as chiral auxiliaries: synthesis of enantiomerically pure β-lactones. First International Electronic Conference on Synthetic Organic Chemistry (ECSOC-1) 1997.
13. Solladié-Cavallo, A.; Solladié, G.; Tsamo, E. Chiral (Arene)tricarbonylchromium Complexes: Resolution of Aldehydes. J. Org. Chem. 1979, 44, 4189-4191.
14. Top, S.; Jaouen, G.; Baldoli, C.; Del Buttero, P.; Maiorana, S. Microbial resolution of organometallic planar chirality. Enantioselective reduction of ortho and meta-substituted tricarbonylchromium benzaldhydes by bakers' yeast. J. Organomet. Chem. 1991, 413, 125-135.
15. Mulzer, J.; Segner, J.; Brüntrup, G. Stereoselective synthesis of threo 3-hydroxycarboxylic acids. Stereochemistry of an aldol type addition under kinetic and thermodynamic control. Tetrahedron Lett. 1977, 52, 4651-4654.
16. Mulzer, J.; Zippel, M.; Brüntrup, G.; Segner, J.; Finke, J. Stereochemistry of the addition of carboxylic acid dianions to aldehydes under kinetic and thermodynamic control. Synthesis and configurational assignment of 2,3-disubstituted threo- and erythro-3-hydroxycarboxylic acids. Liebigs Ann. Chem. 1980, 1108-1134.
17. Canceill, J.; Basselier, J.J.; Jacques, J. Sur la stéré ochimie de la réaction de Réformatsky. Spectres IR et spectres de RMN des β-hydroxyesters obtenus. Dosage de leurs mélanges. Bilan des résultats. Bull. Chim. Soc. Fr. 1967, 3, 1024-1030.
18. Adam, W.; Baeza, J.; Liu, J.C. Stereospecific introduction of double bonds via thermolysis of β-lactones. J. Am. Chem. Soc. 1972, 94, 2000-2006.
19. Mulzer, J.; Pointner, A.; Chucholowski, A.; Brüntrup, G. Threo 3-hydroxycarboxylic acids as key intermediates in a highly stereoselective synthesis of (Z) and (E)-olefins and enol ethers. J. Chem. Soc. Chem. Commun. 1979, 52-54, and ref. therein.
20. Solladié-Cavallo, A. Chiral arene-chromium-carbonyl complexes in asymmetric synthesis. Adv. Met.-Org. Chem. 1989, 1, 99-133.