The reaction of (S)-3-N-Cbz-4-pentenoic acid with iodine in acetonitrile in the presence of AgOTf gave the cis-iodo-lactone 6 in excellent yield and in a highly diastereoselective manner. The substitutions of the iodine in 6 by different Grignard reagents in the presence of CuI and the subsequent conversions into the functionalized syn-γ-hydroxy-β-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 gamma-hydroxy beta-amino acids / G., DELLE MONACHE; Misiti, Domenico; P., Salvatore; G., Zappia. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - STAMPA. - 11:(1999), pp. 1137-1149. [10.1016/S0957-4166(00)00033-1]
Iodolactonization of 3-amino 4-pentenoic acid: a stereoselective synthesis of syn gamma-hydroxy beta-amino acids
MISITI, Domenico;
1999
Abstract
The reaction of (S)-3-N-Cbz-4-pentenoic acid with iodine in acetonitrile in the presence of AgOTf gave the cis-iodo-lactone 6 in excellent yield and in a highly diastereoselective manner. The substitutions of the iodine in 6 by different Grignard reagents in the presence of CuI and the subsequent conversions into the functionalized syn-γ-hydroxy-β-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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
