期刊
TETRAHEDRON-ASYMMETRY
卷 23, 期 2, 页码 157-163出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2012.01.013
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资金
- University of Akureyri
- Rannis
The tin(II) bromide catalyzed reaction of diazofluorene with racemic propane-1,2-diol in 1,2-dimethoxymethane gave the 1- and 2-monoethers in similar amounts. After tritylation of the 2-ether, 2-(9H-fluoren-9-yloxy)-1-triphenylmethyloxypropane and 1-(9H-fluoren-9-yloxy)propan-2-ol were obtained in pure form. The enantiomeric 1-fluorenyl ethers were resolved by kinetic resolution by transacetylation with the help of Pseudomonas cepacia lipase and both enantiomers of the propane-1,2-diol were obtained after deprotection. The racemic 2-(9H-fluoren-9-yloxy)propan-1-ol was obtained after de-triphenylmethylation. However, transacetylation onto this alcohol under identical conditions to those used for the 1-fluorenyl ether showed no enantioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.
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