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 H-1 NMR and molecular modeling. A novel method using an atropisomeric dicarboxylic acid as a chiral solvating agent in H-1 NMR for the determination of the enantiomeric excess of the products is also reported. (C) 2002 Elsevier Science Ltd. All rights reserved.
Optical Resolution and Enantioselective Rearrangements of Amino Group Containing Oxiranyl Ethers
Mordini Alessandro
2002
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 H-1 NMR and molecular modeling. A novel method using an atropisomeric dicarboxylic acid as a chiral solvating agent in H-1 NMR for the determination of the enantiomeric excess of the products is also reported. (C) 2002 Elsevier Science Ltd. All rights reserved.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
