281208-45-5Relevant academic research and scientific papers
Diastereoselective synthesis of cyclic β2,3-amino acids utilizing 4-substituted-1,3-oxazinan-6-ones
Sleebs, Brad E.,Nguyen, Nghi H.,Hughes, Andrew B.
supporting information, p. 6275 - 6284 (2013/07/27)
The 4-substituted-1,3-oxazinan-6-one scaffold is a versatile synthon enabling access to a diverse array of β-amino acid derivatives. In this study, the synthetic utility of the 1,3-oxazinan-6-one is expanded to include the diastereoselective synthesis of
Iodolactonization of 3-amino-4-pentenoic acid: a stereoselective synthesis of syn-γ-hydroxy-β-amino acids
Monache, Giuliano Delle,Misiti, Domenico,Salvatore, patrizia,Zappia, Giovanni
, p. 1137 - 1149 (2007/10/03)
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.
