Di-tert-butyl dicarbonate: a versatile carboxylating reagent

Tetrahedron

Volumn 65, Issue 1, 2009, Pages 134-138

  Augustine, John Kallikat ^a,b   Arthoba Naik, Y ^b   Vairaperumal, Veeramani ^a   Narasimhan, Sharmila ^a  

^a SYNGENE INTERNATIONAL LTD   (India)

^b KUVEMPU UNIVERSITY   (India)

Author keywords

Boc anhydride; Carbon nucleophile; Carboxylating reagent; Di tert butyl malonate; Non nucleophilic base

Indexed keywords

ACETIC ACID DERIVATIVE; BENZOIC ACID DERIVATIVE; CARBONIC ACID DERIVATIVE; DI TERT BUTYL (2 BROMOPYRIDIN 4 YL)MALONATE; DI TERT BUTYL (2 FLUOROPYRIDIN 4 YL)MALONATE; DI TERT BUTYL(PYRIDIN 2 YL)MALONATE; DI TERT BUTYLDICARBONATE; MALONIC ACID; REAGENT; TERT BUTYL (2 BROMOPYRIDIN 4 YL)ACETATE; TERT BUTYL (2 FLUOROPYRIDIN 4 YL)ACETATE; TERT BUTYL (3,5 DIMETHYLPYRIDIN 2 YL)ACETATE; TERT BUTYL (4 BROMOPHENYL)(CYANO)ACETATE; TERT BUTYL (6 CHLORO 5 CYANOPYRIDIN 2 YL)ACETATE; TERT BUTYL (6 CHLOROPYRIDIN 2 YL)ACETATE; TERT BUTYL (8 CHLOROQUINOLIN 2 YL)ACETATE; TERT BUTYL 2 PYRAZIN 2 YLPROPANOATE; TERT BUTYL 3 BROMO 2,6 DIMETHOXYBENZOATE; TERT BUTYL 3 BROMO 5 FLUOROISONICOTINATE; TERT BUTYL 4 BROMO 2,6 DIFLUOROBENZOATE; TERT BUTYLCYANO (2,4 DIFLUOROPHENYL)ACETATE; TERT BUTYLCYANO (3 METHOXYPHENYL)ACETATE; TERT BUTYLCYANO (4 NITROPHENYL)ACETATE; TERT BUTYLCYANO [4 (TRIFLUOROMETHOXY)PHENYL]ACETATE; TERT BUTYLMETHYL (3,5 DIMETHOXYPHENYL)MALONATE; TERT BUTYLMETHYL (3,5 DIMETHYLPHENYL)MALONATE; TERT BUTYLMETHYL 2 THIENOMALONATE; TERT BUTYLMETHYL [3 (TRIFLUOROMETHYL)PHENYL]MALONATE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CARBOXYLATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 56949086445     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.10.089     Document Type: Article

References (25)

1. For N-BOC protection, see:. Greene T.W., and Wuts P.G.M. Protective Group in Organic Synthesis. 3rd ed. (1999), Wiley, New York, NY pp 518-525
2. Wakselman M. In: Paquette L.A. (Ed). Encyclopedia of Reagents for Organic Synthesis Vol. 3 (1995), John Wiley and Sons, New York, NY 1602-1608 and references therein
3. Knölker H.-J., Braxmeier T., and Schlechtingen G. Angew. Chem. 107 (1995) 2746-2749
4. Angew. Chem., Int. Ed. Engl. 34 (1995) 2497-2500
5. Knölker H.-J., Braxmeier T., and Schlechtingen G. Synlett (1996) 502-504
6. Knölker H.-J., and Braxmeier T. Tetrahedron Lett. 37 (1996) 5861-5864
7. Knölker H.-J., and Braxmeier T. Tetrahedron Lett. 39 (1998) 9407-9410
8. Pozdnev V.F. Tetrahedron Lett. 36 (1995) 7115-7118
9. Pozdnev V.F. Int. J. Pept. Protein Res. 44 (1994) 36-48
10. Takeda K., Akiyama A., Nakamura H., Takizawa S., Mizuno Y., Takayanagi H., and Harigaya Y. Synthesis (1994) 1063-1066
11. Basel Y., and Hassner A. Synthesis (1997) 309-312
12. Mattern R.-H. Tetrahedron Lett. 37 (1996) 291-294
13. Nagarajan M., Kumar V.S., and Rao B.V. Tetrahedron Lett. 38 (1997) 5835-5838
14. Mohapatra D.K., and Datta A. Synlett (1996) 1129-1130
15. Mohapatra D.K., and Datta A. Bioorg. Med. Chem. Lett. 7 (1997) 2527-2530
16. Hongmei L., and Jaume B. Tetrahedron Lett. 49 (2008) 2034-2037
17. For examples of carbanion generation using LDA and their reaction with electrophiles:
18. Hiyoshizo K., Hiroyuki H., Hirotaka T., Masahiro W., and Motoo S. Tetrahedron: Asymmetry 9 (1998) 3203-3212
19. Swaminathan R.N., Meng-Hsin C., Stephen T.H., Robert M.T., Ellen M.C., Cui M., Han K., Jingchao D., Bin H., Wu H., and Shu-Hui C. Tetrahedron Lett. 47 (2006) 5063-5067
20. Liusheng Z., Marc V., Sean P.B., and Julio C.M. Tetrahedron Lett. 49 (2008) 1768-1770
21. Sumalee K., Rachel Q., Netnapa C., Rachel P., Tirayut V., Jarunee V., Bongkoch T., Worachart S., Gordon L., and Yongyuth Y. J. Med. Chem. 47 (2004) 673-680
22. Bongkoch T., Chawanee S., Worrapong P., Chakapong I., Worachart S., Sumalee K., Jarunee V., Yodhathai T., and Yongyuth Y. J. Med. Chem. 45 (2002) 1244-1252
23. Toshiyuki I., Keiko K., Miki T., and Yumiko T. J. Org. Chem. 56 (1991) 797-804
24. Gu Y.G., and Bayburt E.K. Tetrahedron Lett. 37 (1996) 2565-2568
25. Commercial LDA was found to provide quantitative yields when used in slight excess (1.4 equiv).