Mild reduction of carboxylic acids to alcohols using cyanuric chloride and sodium borohydride

Tetrahedron Letters

Volumn 40, Issue 23, 1999, Pages 4395-4396

  Falorni, Massimo ^a   Porcheddu, Andrea ^a   Taddei, Maurizio ^a  

^a UNIVERSITY OF SASSARI   (Italy)

Author keywords

Alcohols; Amino acids; Carboxylic acids; Reduction

Indexed keywords

ALCOHOL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CHLORIDE; CYANURIC ACID; SODIUM BOROHYDRIDE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; STEREOCHEMISTRY;

EID: 0033523061     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00734-0     Document Type: Article

References (8)

1. Larock, R.C. Comprehensive Organic Transformations, VCH: New York, 1989: 548.
2. Abiko, A.; Masamune, S. Tetrahedron Lett. 1992, 33, 5517
3. Kokotos, G. Synthesis, 1990, 299. Rodriguez, M.; Llinares, M.; Doulut, S.; Heitz, A.; Martinez, J.Tetrahedron Lett. 1991, 32, 923.
4. Kokotos, G. Synthesis, 1990, 299. Rodriguez, M.; Llinares, M.; Doulut, S.; Heitz, A.; Martinez, J. Tetrahedron Lett. 1991, 32, 923.
5. McGeary, R.P. Tetrahedron Lett. 1998, 39, 3319.
6. Cyanuric chloride, price about 5.5 Euro per mol. BOP reagent, price about 19000 Euro per mol. Source: The Aldrich Catalogue, 1999-2000, prices in Italian Lira.
7. St-Denis, Y.; Chan, T-H. J. Org. Chem. 1992, 57, 3078
8. The absence of racemisation suggested that the intermediate 2 is formed instead of the corresponding acyl chloride as reported by: Venkataram, K.; Wagle, D.R.; Tetrahedron Lett. 1979, 32, 3037.