Asymmetric Synthesis of Chiral gamma- and delta-Amino Esters Using Trichlorosilane Activated with a Lewis Base Catalyst
CHEMISTRYSELECT, vol.5, pp.6035-6039, 2020 (SCI-Expanded, Scopus)
- Publication Type: Article / Article
- Volume: 5
- Publication Date: 2020
- Doi Number: 10.1002/slct.202000790
- Journal Name: CHEMISTRYSELECT
- Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier
- Page Numbers: pp.6035-6039
- Keywords: Asymmetric synthesis, Lewis bases, Optically active amino esters, Organocatalyst, HIGHLY ENANTIOSELECTIVE REDUCTION, ACID METHYL-ESTER, X-RAY-CRYSTAL, N-ARYL IMINES, NMR-SOLUTION, HYDROSILYLATION, HYDROGENATION, DERIVATIVES, FORMAMIDE, ORGANOCATALYST
- Istanbul University-Cerrahpasa Affiliated: Yes
Abstract
Novel chiral gamma- and delta- amino esters 2 a-k were synthesized by enantioselective reduction of N-aryl gamma- and delta-imino esters with aryl, substituted aryl, and heteroaryl groups 1 a-k using trichlorosilane activated with optically active N-pivaloyl L-proline I in high yields (50%-98%) with enantioselectivities (10%-84% enantiomeric excess). The structures of the chiral amino esters 2 a-k were clarified by infrared, nuclear magnetic resonance (H-1 and C-13) and gas chromatography-mass spectrometry. The enantiomeric excess of these compounds were identified by chiral high-performance liquid chromatography using a Chiralpak AD-H column. The highest ee of 84% and highest yield of 98% were found for 2 d.