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Stereoselective synthesis of (+)-flutriafol
- Authors
- Chang, Minsun; Kim, Tae Hyun; Kim, Hee-Doo
- Issue Date
- 30-Jun-2008
- Publisher
- PERGAMON-ELSEVIER SCIENCE LTD
- Citation
- TETRAHEDRON-ASYMMETRY, v.19, no.12, pp 1504 - 1508
- Pages
- 5
- Journal Title
- TETRAHEDRON-ASYMMETRY
- Volume
- 19
- Number
- 12
- Start Page
- 1504
- End Page
- 1508
- ISSN
- 0957-4166
1362-511X
- Abstract
- The stereoselective synthesis of (+)-flutriafol, a triazole fungicide, has been accomplished in seven linear steps from (1S)-[(4R)-2,2-dimethyl-[1,3]-dioxotan-4-yl]-(4-methoxyphenyl)methanol in 15% overall yield. Diastereoselective nucleophilic 1,2-addition was employed as a key step for constructing the requisite chiral 1,2-diol for flutriafol. A high degree of 1,4-asymmetric induction could be realized via a chelation-controlled mechanism during the key alkylation step. (C) 2008 Elsevier Ltd. All rights reserved.
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