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Asymmetric Synthesis of Chiral γ‐ and δ‐Amino Esters Using Trichlorosilane Activated with a Lewis Base Catalyst
Author(s) -
Hasdemir Belma,
Yaşa Hasniye,
Yıldız Tülay,
Küçük Hatice Başpınar,
Onar Hülya Çelik
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202000790
Subject(s) - trichlorosilane , chemistry , enantioselective synthesis , enantiomer , enantiomeric excess , catalysis , aryl , yield (engineering) , lewis acids and bases , organic chemistry , medicinal chemistry , alkyl , materials science , silicon , metallurgy
Novel chiral γ‐ and δ‐ amino esters 2 a – k were synthesized by enantioselective reduction of N ‐aryl γ‐ and δ‐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 ( 1 H and 13 C) 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 .