Template-promoted dimerization of C-allylglycine: A convenient synthesis of (S,S)-2,7-diaminosuberic acid

Tetrahedron Letters

Volumn 39, Issue 13, 1998, Pages 1689-1690

  O'Leary, Daniel J ^a,b   Miller, Scott J ^a,c   Grubbs, Robert H ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

^b POMONA COLLEGE   (United States)

^c BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCINE DERIVATIVE;

ARTICLE; DIMERIZATION; DNA TEMPLATE; DRUG SYNTHESIS; GEL CHROMATOGRAPHY; HYDROGENATION; MOLECULAR RECOGNITION; NONHUMAN; PROTEIN SECONDARY STRUCTURE;

EID: 0032568262     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00126-9     Document Type: Article

References (11)

1. 3. Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 3800-3801, and references within.
2. 4. For recent reviews, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452.
3. (b) Schmalz, H.-G. Angew. Chem. Int. Ed. Engl. 1995, 34, 1833-1836.
4. 5. Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606-9614.
5. 6. For asymmetric syntheses of 7, see: (a) Williams, R. M.; Yuan, C. J. Org. Chem. 1992, 57, 6519-6527.
6. (b) Nutt, R. F.; Strachan, R. G.; Veber, D. F.; Holly, F. W. J. Org. Chem. 1980, 45, 3078-3080.
7. 7. Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. J. Am. Chem. Soc. 1997, 119, 656-673.
8. 8. Chenault, H. K.; Dahmer, J.; Whitesides, G. M. J. Am. Chem. Soc. 1989, 111, 6354-6364.
9. 9. Cox, R. J.; Sherwin, W. A.; Lam, L. K. P.; Vederas, J. C. J. Am. Chem. Soc. 1996, 118, 7449-7460.
10. 10. Diver, S. T.; Schreiber, S. L. J. Am. Chem. Soc. 1997, 119, 5106-5109.
11. 6b +41.8° (c 0.2, 6 N HCl)], Efforts are currently underway to assess the enantiomeric purity of the product.