The reaction of (S)-3-N-Cbz-4-pentenoic acid with iodine in acetonitrile in the presence of AgOTf gave the corresponding cis-iodo-lactone in excellent yield and in a highly diastereo-selective manner. The substitutions of the iodine by different Grignard reagents in the presence of CuI and the subsequent conversions into the functionalized syn-g-hydroxy-b-amino acids have been investigated. By the above reaction sequence, (3S,4S)-3-amino-4-hydroxy-5-cyclohexyl pentanoic acid was synthesized with high enantioselectivity.
iodolactonization of 3-amino 4-pentenoic acid: a stereoselective synthesis of syn-g-hydroxy b-amino acids
ZAPPIA, GIOVANNI
2000
Abstract
The reaction of (S)-3-N-Cbz-4-pentenoic acid with iodine in acetonitrile in the presence of AgOTf gave the corresponding cis-iodo-lactone in excellent yield and in a highly diastereo-selective manner. The substitutions of the iodine by different Grignard reagents in the presence of CuI and the subsequent conversions into the functionalized syn-g-hydroxy-b-amino acids have been investigated. By the above reaction sequence, (3S,4S)-3-amino-4-hydroxy-5-cyclohexyl pentanoic acid was synthesized with high enantioselectivity.File in questo prodotto:
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