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New chiral morpholine-pyrrolidine ligands affecting asymmetric selectivity in copper catalyzed Henry reaction

Author:
Angamuthu, Venkatachalam, Tai, Dar-Fu
Source:
Tetrahedron letters 2019 v.60 no.9 pp. 653-659
ISSN:
0040-4039
Subject:
alcohols, aldehydes, chemical reactions, copper, enantioselectivity, ligands, moieties, morpholine
Abstract:
In this study, several chiral diamine (35, 36, 37 and 39), triamine (24 and 25), diaminol (38, 42 and 43) and triaminol ligands (29 and 30) having chiral morpholine and pyrrolidine moieties conjugated constitutes, were prepared from commercially available (S)-2-amino-2-phenylacetic acid and (S)-proline. These ligands were complexed with copper (II) salt in situ and applied to asymmetricHenry reaction. Asymmetric addition of various structurally divergent aldehydes and nitromethane in the presence of 5 mol% of chiral ligand with CuCl2 furnished corresponding β-nitro alcohol in good yields (up to 55–79%) with good enantioselectivity (up to 89%).
Agid:
6290072