Development of a new dimeric cyclophane ligand: Application to enhanced diastereo- and enantioselectivity in the catalytic synthesis of β-lactams

Journal of Organic Chemistry

Volumn 69, Issue 13, 2004, Pages 4531-4533

  Wack, Harald ^a   France, Stefan ^a   Hafez, Ahmed M ^a   Drury III, William J ^a   Weatherwax, Anthony ^a   Lectka, Thomas ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CATALYST ACTIVITY; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CYCLOPHANE; ENANTIOSELECTIVITY;

DIMERS;

BETA LACTAM DERIVATIVE; CYCLOPHANE DERIVATIVE; DIMER;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHIRALITY; DIASTEREOISOMER; ENANTIOSELECTIVITY; ISOMERIZATION; REACTION ANALYSIS;

CATALYSIS; DIMERIZATION; ETHERS, CYCLIC; LACTAMS; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NAPHTHOLS; STEREOISOMERISM;

EID: 3042778834     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049804d     Document Type: Article

References (15)

1. For some examples of the use of cyclophanes as ligands, see: (a) Worsdorfer, U.; Vögtle, F.; Nieger, M.; Waletzke, M.; Grimme, S.; Glorius, F.; Pfaltz, A. Synthesis 1999, 4, 597-602.
2. (b) Hou, X.-L.; Wu, X.-W.; Dai, L.-X.; Cao, B.-X.; Sun, J. Chem. Commun. 2000, 1195-1196.
3. (c) Dahmen, S.; Brase, S. Chem. Commun. 2002, 26-27.
4. (d) Inoue, M. B.; Velazquez, E. F.; Medrano, F.; Ochoa, K. L.; Galvez, J. C.; Inoue, M.; Fernando, Q. Inorg. Chem. 1998, 87, 4070-4075.
5. (e) Pye, P. J.; Rossen, K.; Reamer, R, A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207-6208.
6. Hopf, H.; Grahn, W.; Barrett, D. G.; Gerdes, A.; Hillmer, J.; Hucker, J.; Y. O.; Kaida, Y. Chem. Ber. 1990, 123, 841-845.
7. Pamperin, D.; Schulz, C.; Hopf, H.; Syldatk, C.; Pietzsch, M. Eur. J. Org. Chem. 1998, 7, 1441-1446.
8. Whitesides, G. M.; SanFilippo, J. J.; Casy, C. P.; Panek, E. J. J. Am. Chem. Soc. 1967, 89, 5302-5303.
9. p represents the stereochemistry about the pivot bond (pivot or axial isomers); and C represents the configuration of the second cyclophane moiety.
10. p,R) enantiomer in identical yield.
11. We used the program Macromodel (version 7.0) for the calculations (Schrodinger, Inc.).
12. Calculations were performed using the Titan Program, version 2.0.
13. France, S.; Wack, H.; Hafez, A. M.; Taggi, A. E.; Witsil, D. R.; Lectka, T. Org. Lett. 2002, 4, 1603-1605 and references therein.
14. 3 was used as the cocatalyst without BINOL ligand, lactam product was formed in 75% yield with 11:1 dr and 99% ee.
15. Firestone, R. A.; Barker, P. L.; Pisano, J. M.; Ashe, B. M.; Dahlgren, M. E. Tetrahedron 1990, 46, 2255-2262.