Asymmetric Alkylation of tert-Butyl Glycinate Schiff Base with Chiral Quaternary Ammonium Salt under Micellar Conditions
- 7 April 2001
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 3 (10) , 1515-1517
- https://doi.org/10.1021/ol015829c
Abstract
The asymmetric alkylation of the tert-butyl glycinate−benzophenone Schiff base 1 with various arylmethyl bromides catalyzed by O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide (2) proceeded smoothly under micellar conditions (5 equiv of 1 M KOH and 0.4 equiv of Triton X-100) to give the alkylated products in good yields and with good enantioselectivity (72−85% ee), depending on the electrophiles.Keywords
This publication has 5 references indexed in Scilit:
- Catalytic asymmetric alkylation in aqueous micellesTetrahedron Letters, 2000
- Poly(ethylene glycol) as solvent and polymer support in the microwave assisted parallel synthesis of aminoacid derivativesTetrahedron Letters, 2000
- Accelerated Biphasic Hydroformylation by Vesicle Formation of Amphiphilic DiphosphinesJournal of the American Chemical Society, 2000
- Phase-transfer catalyzed asymmetric Darzens reaction of cyclic α-chloro ketonesChemical Communications, 1999
- New Strategies to α‐Alkylated α‐Amino AcidsAngewandte Chemie International Edition in English, 1997