Sodium borohydride-mediated transesterification

Synthetic Communications

Volumn 40, Issue 9, 2010, Pages 1312-1321

  Sereda, Grigoriy ^a   Pothula, Swetha ^a   Dreessen, James ^a  

^a W O Farber Center for Civic Leadership   (United States)

Author keywords

Esterification; Reduction; Selectivity; Synthesis; Thioesters

Indexed keywords

ALCOHOL; BASE; BORIC ACID; DICHLOROMETHANE; DICYCLOHEXYLCARBODIIMIDE; ESTER DERIVATIVE; N,N DIMETHYLFORMAMIDE; SODIUM BOROHYDRIDE; SODIUM TETRAALKOXYBORATE; SOLVENT; THIOESTER; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE; SENSITIVITY ANALYSIS; TRANSESTERIFICATION;

EID: 77951079209     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903072438     Document Type: Article

References (25)

1. 2. Tetra-hedron Lett. 2008, 49(6), 996-999.
2. Otera, J. Transesterification. Chem. Rev. 1993, 93, 1449-1470.
3. 1H FTNMR Spectra, 1st ed.; Aldrich Chemical Company Inc.: Milwaukee, WI, 1993; vol.2, p. 326B.
4. 1H FTNMR Spectra, 1st ed.; Aldrich Chemical Company Inc.: Milwaukee, WI, 1993; vol.2, p. 1240B.
5. 1H FTNMR Spectra, 1st ed.; Aldrich Chemical Company Inc.: Milwaukee, WI, 1993; vol.2, p. 1262C.
6. 1H FTNMR Spectra, 1st ed.; Aldrich Chemical Company Inc.: Milwaukee, WI, 1993; vol.2, p. 1267A.
7. 1H FTNMR Spectra, 1st ed.; Aldrich Chemical Company Inc.: Milwaukee, WI, 1993; vol.2, p. 697C.
8. Ranu, B. C.; Dutta, P.; Sarkar, A. A simple and efficient procedure for transesterification catalyzed by indium triiodide. J. Org. Chem. 1998, 63, 6027-6028.
9. Frank, R. L.; Davis, H. R. Jr.; Drake, S. S.; McPherson, J. B. Jr. Ester interchange by means of the Grignard complex. J. Am. Chem. Soc. 1944, 66, 1509-1510.
10. Brown, H. C.; Mead, E. J. The preparation and properties of sodium tetraalkoxyboro-hydrides. J. Am. Chem. Soc. 1956, 78, 3614-3616.
11. Wigfield, D. C. Stereochemistry and mechanism of ketone reductions by hydride reagents. Tetrahedron 1979, 35(4), 449-462.
12. Kayser, M. M.; Eliev, S.; Eisenstein, O. Reduction of ketones by sodium borohydride in the absence of protic solvents: Inter versus intramolecular mechanism. Tetrahedron Lett. 1983, 24(10), 1015-1018.
13. 1H FTNMR Spectra, 1st ed.; Aldrich Chemical Company Inc.: Milwaukee, WI, 1993; vol.2, p. 922A.
14. 1H FTNMR Spectra, 1st ed.; Aldrich Chemical Company Inc.: Milwaukee, WI, 1993; vol.2, p. 165B.
15. Dickes, E.; Turgeon, A.; Sereda, G. A. Synthesis of the adduct of 1,8-dimethoxyanthra-cene and maleic anhydride as a convenient intermediate toward new bicyclic diquinones. J. Undergrad. Chem. Res. 2009, 8(2), 49-51.
16. Liu, H. J.; Bukownik, R. R.; Pednekar, P. R. Selective reduction of thiol esters with sodium borohydride. Synth. Commun. 1981, 11(8), 599-603.
17. 4. Sulfur Lett. 1982, 1, 69-78.
18. Dahmen, J.; Frejd, T.; Magnusson, G.; Noori, G.; Carlstroem, A. S. Synthesis from pullulan of spacer-arm lipid, and ethyl glycosides of a tetrasaccharide (a-D-GLc-(1-6)-a-D-GLc-(1-D-GLc(1-4)-D-GLc) found in human urine: Preparation of neoglycoproteins. Carbohydrate Res. 1984, 127, 27-33.
19. Koenig, N. H.; Sasin, G. S.; Swern, D. Organic sulfur derivatives, V: Preparation and properties of some long-chain mercapto acids and related compounds. J. Org. Chem. 1958, 23, 1525-1530.
20. Humphrey, R. E.; Potter, J. L. Reduction of disulfides with tributylphosphine. Anal. Chem. 1965, 37(1), 164-165.
21. Belser, T.; Stohr, M.; Pfaltz, A. Immobilization of rhodium complexes at thiolated monolayers on gold surfaces: Catalytic and structural studies. J. Am. Chem. Soc. 2005, 127, 8720-8731. (Pubitemid 40868255)
22. Kleinert, M.; Rockendorf, N.; Lindhorst, T. K. Glyco-SAMs as glycocalyx mimetics: Syn-thesis of L-fucose-and D-mannose-terminated building blocks. Eur. J. Org. Chem. 2004, 3931-3940.
23. Bader, M. M. Synthesis and characterization of terminally functionalized n-alkanethiols. Phosphorous, Sulfur Silicon Relat. Elem. 1996, 116, 77-92. (Pubitemid 127036411)
24. Cunneen, J. I.; Moore, C. G.; Shephard, B. R. New methods of crosslinking natural rubber, part I: The introduction of carboxylic acid and ester groups into natural rubber and their subsequent utilization for crosslinking. J. Appl. Polym. Sci. 2003, 3(7), 11-19
25. We employed a procedure similar to the immobilization of 6-acetylthiohexanoic acid: Worden, J. G.; Dai, Q.; Shaffer, A. W.; Huo, Q. Monofunctional group-modified gold nanoparticles from solid phase synthesis approach: Solid support and experimental con-dition effect. Chem. Mater. 2004, 16, 3746-3755.