Asymmetric Synthesis of Chiral gamma- and delta-Amino Esters Using Trichlorosilane Activated with a Lewis Base Catalyst


Hasdemir B. , Yasa H. , Yildiz T. , Kucuk H. , Onar H.

CHEMISTRYSELECT, cilt.5, ss.6035-6039, 2020 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 5 Konu: 20
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1002/slct.202000790
  • Dergi Adı: CHEMISTRYSELECT
  • Sayfa Sayıları: ss.6035-6039

Özet

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.