Kinetic Resolution of rac-4,12-Dibromo[2.2]paracyclophane in a Palladium [2.2]PHANEPHOS Catalyzed Animation

Journal of Organic Chemistry

Volumn 62, Issue 19, 1997, Pages 6462-6463

  Rossen, Kai ^a   Pye, Philip J ^a   Maliakal, Ashok ^a   Volante, R P ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001054296     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971300a     Document Type: Article

References (18)

1. (a) Lüttringhaus, A.; Gralheer, H. Justus Liebigs Ann. Chem. 1942, 550, 67.
2. (b) Cram, D. J.; Allinger, N. L. J. Am. Chem. Soc. 1955, 77, 6289.
3. (a) Bodwell, G. J. Angew. Chem., Int. Ed. Engl. 1996, 35, 2085.
4. (b) Togni, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1475
5. (c) Dosa, I. P.; Ruble, J. C.; Fu, G. C. J. Org. Chem. 1997, 62, 444.
6. Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207.
7. Pye, P. J.; Rossen, K.; Reamer, R. A.; Volante, R. P.; Reider, P. J. Manuscript in preparation.
8. (a) Marcoux, J.-F.; Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1568.
9. (b) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215.
10. (c) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217.
11. The oxidation of the benzylic position in these amines takes place in the presence of air. The imine resulting from this oxidation can be isolated when the reaction is performed with α-methylbenzylamine.
12. Lindner, W. In Methods of Organic Chemistry (Houben Weyl), Stereoselective Synthesis; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme Verlag, Stuttgart, 1996; Vol. E21, Chapt. 3.1.6.
13. (a) Kagan, H. B.; Fiaud, J. C. in Topics in Stereochemistry, Eliel, E. L., Wilen, S. H., Eds.; Wiley: New York, 1988, Vol. 18, p 249.
14. Overman, L. E.; Poon, D. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 518.
15. Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237.
16. 2 with MeOH modifier gradient: 4 min at 4% and then ramping up to 36% within 32 min, flow 1 mL/min, Retention times (R)-2: 22.6 min, (S)-2: 25.5 min.
17. (a) The absolute configuration of (R)-2 and (S)-2 are known by correlation with the bisphosphine oxide of [2.2]PHANEPHOS, whose absolute configuration was determined by X-ray crystallography as a complex with dibenzoyl-D-tartaric acid. See also ref 3.
18. (b) M. D. Fryzuk, B. Bosnich J. Am. Chem. Soc. 1978, 100, 5491.