Highly enantioselective synthesis of 5-phenyl-2-alkylprolines using phase-transfer catalytic alkylation SCIE SCOPUS

Cited 17 time in WEB OF SCIENCE Cited 17 time in Scopus
Title
Highly enantioselective synthesis of 5-phenyl-2-alkylprolines using phase-transfer catalytic alkylation
Author(s)
Lee, Myungmo; Lee, Young-Ju; Park, Eunyoung; Park, Yohan; Ha, Min Woo; Hong, Suckchang; Lee, Yeon-Ju; Kim, Taek-Soo; Kim, Mi-hyun; Park, Hyeung-geun
KIOST Author(s)
Lee, Yeon Ju(이연주)
Publication Year
2013
Abstract
An efficient enantioselective synthetic method for the synthesis of (2R)-5-phenyl-2-alkylproline tert-butyl esters was reported. The phase-transfer catalytic alkylation of tert-butyl-5-phenyl-3,4-dihydro-2H-pyrrole-2-carboxylate in the presence of chiral quaternary ammonium catalysts gave the corresponding alkylated products (up to 97% ee). The following diastereoselective reductions afforded chiral 5-phenyl-2-alkylprolines which can be applied to asymmetric synthesis as organocatalysts or synthesis of biologically active proline based compounds, such as chiral a-alkylated analogues of (+)-RP66803, as potential CCK antagonists.
ISSN
1477-0520
URI
https://sciwatch.kiost.ac.kr/handle/2020.kiost/3320
DOI
10.1039/c3ob27089k
Bibliographic Citation
ORGANIC & BIOMOLECULAR CHEMISTRY, v.11, no.12, pp.2039 - 2046, 2013
Publisher
ROYAL SOC CHEMISTRY
Subject
1,3-DIPOLAR CYCLOADDITION; ASYMMETRIC-SYNTHESIS; AZOMETHINE YLIDES; ANALOGS; DESIGN; SALTS; ESTER; ACIDS
Type
Article
Language
English
Document Type
Article
Publisher
ROYAL SOC CHEMISTRY
Files in This Item:
There are no files associated with this item.

qrcode

Items in ScienceWatch@KIOST are protected by copyright, with all rights reserved, unless otherwise indicated.

Browse