Controlled synthesis of asymmetric dialkyl and cyclic carbonates using the highly selective reactions of imidazole carboxylic esters

Organic Letters

Volumn 1, Issue 6, 1999, Pages 933-936

  Rannard, Steve P ^a,b   Davis, Nicola J ^a,c  

^a C ^*  (United Kingdom)

^b UNILEVER RESEARCH   (United Kingdom)

^c UNIVERSITY OF READING   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002300688     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9908528     Document Type: Article

References (11)

1. Yu, B.; Zhang, J.; Lu, S.; Hui, Y. Synlett 1998, 29 and papers cited therein.
2. (a) Pulido, R.; Gotor, V. Carbohydr. Res. 1994, 252, 55.
3. (b) Braun, P.; Waldmann, H.; Vogt, W.; Kunz, H. Liebigs Ann. Chem. 1991, 2, 165.
4. (a) Happaerts, T.; Ghosez, L. Org. Synth. 1998, 75, 177.
5. (b) Toste, F. D.; Still, W. J. Synlett 1995, 159.
6. (c) Bose, D. S.; Lakshminarayana, V. Synthesis 1999, 66.
7. Cotarca, L.; Delogu, P.; Nardelli, A.; Sunjic, V. Synthesis 1996, 553.
8. Staab, H. A. Angew. Chem., Int. Ed. Engl. 1962, 1, 351.
9. Houlihan, F. M.; Bouchard, F.; Frechet, J. M. J. Macromolecules 1986, 19, 13.
10. +, 100%). When using primary alcohols, a 1.1 molar excess of CDI is added to the flask and the alcohol is added dropwise over a period of at least 30 min.
11. +, 100%). In most cases it is preferable to synthesise the imidazole carboxylic ester in situ (as in ref 7) and add the alcoholic reagent directly to the flask without workup. In this case, 2a would be synthesized and 4 would be directly added to the reaction mixture after 4 h at 60°C.