Racemization in Suzuki couplings: A quantitative study using 4-hydroxyphenylglycine and tyrosine derivatives as probe molecules

Journal of Organic Chemistry

Volumn 72, Issue 3, 2007, Pages 1047-1050

  Prieto, Mònica ^a   Mayor, Silvia ^a   Rodríguez, Katy ^a   Lloyd Williams, Paul ^a   Giralt, Ernest ^a,b  

^a UNIVERSITY OF BARCELONA   (Spain)

^b INSTITUTE FOR RESEARCH IN BIOMEDICINE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID; OPTICAL PURITY; RACEMIZATION; SUZUKI COUPLINGS;

INORGANIC ACIDS; OPTICAL PROPERTIES; SODIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

AMINO ACIDS;

AMINO ACID DERIVATIVE; BORONIC ACID DERIVATIVE; CHLOROPEPTIN; INDOLYLBORONIC ACID DERIVATIVE; OXFENICINE; PEPTIDE DERIVATIVE; SODIUM CARBONATE; SUCCINIC ACID; TYROSINE DERIVATIVE; UNCLASSIFIED DRUG; VANCOMYCIN DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; MOLECULAR PROBE; MOLECULE; QUANTITATIVE ANALYSIS; RACEMIZATION; SUZUKI REACTION;

BORONIC ACIDS; CARBONATES; CYCLIZATION; GLYCINE; MODELS, CHEMICAL; ORGANOMETALLIC COMPOUNDS; SODIUM; SUCCINATES; TYROSINE;

EID: 33846913687     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0621266     Document Type: Article

References (15)

1. Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. Engl. 2005, 44, 4442-4489.
2. Suzuki, A. J. Organomet. Chem. 2002, 653, 83-90.
3. Lloyd-Williams, P.; Giralt, E. Chem. Soc. Rev. 2001, 30, 145-157.
4. Benoiton, N. L. Int. J. Peptide Protein Res. 1994, 44, 399-400.
5. Steinauer, R.; Chen, F. M. F.; Benoiton, N. L. J. Chromatogr. 1985, 325, 111-126.
6. Benoiton, N. L. Chemistry of Peptide Synthesis; CRC Press: Boca Raton, 2006.
7. Lloyd-Williams, P.; Albericio, F.; Giralt, E. Chemical Approaches to the Synthesis of Peptides and Proteins; CRC Press: Boca Raton, 1997.
8. Espuña, G.; Arsequell, G.; Valencia, G.; Barluenga, J.; Pérez, M.; González, J. M. Chem. Commun. 2000, 1307-1308.
9. Espuña, G.; Arsequell, G.; Valencia, G.; Barluenga, J.; Alvarez-Gutierrez, J. M.; Ballesteros, A.; Gonzalez, J. M. Angew. Chem., Int. Ed. Engl. 2004, 43, 325-329.
10. Moyer, M. P.; Shiurba, J. F.; Rapoport, H. J. Org. Chem. 1986, 51, 5106-5110.
11. Prieto, M.; Zurita, E.; Rosa, E.; Muñoz, L.; Lloyd-Williams, P.; Giralt, E. J. Org. Chem. 2004, 69, 6812-6820.
12. Brown, A. G.; Crimmin, M. J.; Edwards, P. D. J. Chem. Soc., Perkin Trans. 1 1992, 123-130.
13. Deng, H. B.; Jung, J. K.; Liu, T.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 9032-9034.
14. Shinohara, T.; Deng, H. B.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2005, 127, 7334-7336.
15. Nicolaou, K. C.; Boddy, C. N. C. J. Am. Chem. Soc. 2002, 124, 10451-10455.