F. Faigl, A. Thurner, G. Tárkányi
Feb 13, 2002
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Influential Citations
14
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Journal
Tetrahedron-asymmetry
Abstract
Abstract Resolution protocols for 2-benzyloxymethyl-3-diethylaminomethyloxirane and 2-benzyloxymethyl-3-piperidinomethyloxirane have been developed. In the presence of organometallic bases enantioselective rearrangement of the newly separated oxirane enantiomers provides chiral oxetanes or cis -but-2-ene-1,4-diol derivatives without any racemization. The stereochemistry of the oxetanes was investigated by 1 H NMR and molecular modeling. A novel method using an atropisomeric dicarboxylic acid as a chiral solvating agent in 1 H NMR for the determination of the enantiomeric excess of the products is also reported.