doi: 10.1021/ar0300625.
The enantioselective synthesis of alpha-amino acids by phase-transfer catalysis with achiral Schiff base esters
Affiliations
- PMID: 15311949
- DOI: 10.1021/ar0300625
Item in Clipboard
The enantioselective synthesis of alpha-amino acids by phase-transfer catalysis with achiral Schiff base esters
Acc Chem Res.
2004 Aug.
Abstract
The development and application of chiral phase-transfer catalysis (PTC) for the enantioselective synthesis of optically active alpha-amino acid derivatives using achiral Schiff base esters developed in the author's laboratory and by others is reviewed. Phase-transfer catalysts derived from the Cinchona alkaloids have been exploited as inexpensive and attractive organocatalysts in the chiral PTC process. The recent evolution and use of these and other catalytic systems is described.
Similar articles
-
Highly practical amino acid and alkaloid synthesis using designer chiral phase transfer catalysts as high-performance organocatalysts.Chem Rec. 2010 Oct;10(5):254-9. doi: 10.1002/tcr.201000019. Chem Rec. 2010. PMID: 20878639 Review.
-
Combinatorial design of simplified high-performance chiral phase-transfer catalysts for practical asymmetric synthesis of alpha-alkyl- and alpha,alpha-dialkyl-alpha-amino acids.Chem Asian J. 2008 Sep 1;3(8-9):1702-14. doi: 10.1002/asia.200800107. Chem Asian J. 2008. PMID: 18683160
-
Highly enantioselective synthesis of (R)-alpha-alkylserines via phase-transfer catalytic alkylation of o-biphenyl-2-oxazoline-4-carboxylic acid tert-butyl ester using cinchona-derived catalysts.Org Lett. 2005 Apr 14;7(8):1557-60. doi: 10.1021/ol050228x. Org Lett. 2005. PMID: 15816751
-
Asymmetric 1,4-addition of oxazolones to nitroalkenes by bifunctional cinchona alkaloid thiourea organocatalysts: synthesis of alpha,alpha-disubstituted alpha-amino acids.Chemistry. 2008;14(35):10958-66. doi: 10.1002/chem.200802030. Chemistry. 2008. PMID: 18979472
-
Catalytic asymmetric direct Mannich reaction: a powerful tool for the synthesis of alpha,beta-diamino acids.Chem Soc Rev. 2009 Jul;38(7):1940-8. doi: 10.1039/b820303b. Epub 2009 Apr 14. Chem Soc Rev. 2009. PMID: 19551174 Review.
Cited by
-
Mechanochemistry assisted asymmetric organocatalysis: A sustainable approach.Beilstein J Org Chem. 2012;8:2132-41. doi: 10.3762/bjoc.8.240. Epub 2012 Dec 6. Beilstein J Org Chem. 2012. PMID: 23243475 Free PMC article.
-
Access to any site directed stable isotope ((2)H, (13)C, (15)N, (17)O and (18)O) in genetically encoded amino acids.Molecules. 2013 Jan 2;18(1):482-519. doi: 10.3390/molecules18010482. Molecules. 2013. PMID: 23282537 Free PMC article. Review.
-
Reactions of Sodium Diisopropylamide: Liquid-Phase and Solid-Liquid Phase-Transfer Catalysis by N,N,N',N″,N″-Pentamethyldiethylenetriamine.J Am Chem Soc. 2021 Aug 25;143(33):13370-13381. doi: 10.1021/jacs.1c06528. Epub 2021 Aug 10. J Am Chem Soc. 2021. PMID: 34375095 Free PMC article.
-
Catalytic Enantioselective Electrophilic Aminations of Acyclic α-Alkyl β-Carbonyl Nucleophilies.Synlett. 2009 Jun;10:1685-1689. doi: 10.1055/s-0029-1217334. Synlett. 2009. PMID: 21340046 Free PMC article.
-
A systematic investigation of quaternary ammonium ions as asymmetric phase-transfer catalysts. Synthesis of catalyst libraries and evaluation of catalyst activity.J Org Chem. 2011 Jun 3;76(11):4260-336. doi: 10.1021/jo2005445. Epub 2011 May 6. J Org Chem. 2011. PMID: 21446721 Free PMC article.
LinkOut - more resources
Full Text Sources
Other Literature Sources
