+ Site Statistics
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

Synthesis of alpha,alpha-disubstituted alpha-amino acid amides by phase-transfer catalyzed alkylation



Synthesis of alpha,alpha-disubstituted alpha-amino acid amides by phase-transfer catalyzed alkylation



Tetrahedron Letters 33(40): 6007-6010



alpha,alpha-Disubstituted alpha-amino acid amides were prepared in 17-86% chemical yield by the phase-transfer catalyzed alkylation of N-benzylidene alpha-H amino acid amides, followed by weak acidic hydrolysis of the Schiff bases.

Please choose payment method:






(PDF emailed within 1 workday: $29.90)

Accession: 009508019

Download citation: RISBibTeXText


Related references

Highly enantioselective phase-transfer-catalyzed alkylation of protected alpha-amino acid amides toward practical asymmetric synthesis of vicinal diamines, alpha-amino ketones, and alpha-amino alcohols. Journal of the American Chemical Society 127(14): 5073-5083, 2005

Synthesis of enantiomerically pure 2,2-disubstituted-2-amino-ethanols by dissolving metal reduction of alpha,alpha-disubstituted amino acid amides. Tetrahedron Letters 35(11): 1777-1780, 1994

Enantioselective synthesis of alpha,alpha-disubstituted alpha-amino acids by Rh-catalyzed cycloaddition of 1,6-diynes with protected dehydroamino acid. Tetrahedron 64(27): 6289-6293, 2008

Alpha-chiral acetylenes having an all-carbon quaternary center: phase transfer catalyzed enantioselective alpha alkylation of alpha-alkyl-alpha-alkynyl esters. Angewandte Chemie 48(27): 5014-5017, 2009

Asymmetric synthesis of alpha,alpha-disubstituted alpha-amino acids by diastereoselective alkylation of camphor-based tricyclic iminolactone. Journal of Organic Chemistry 71(12): 4364-4373, 2006

Asymmetric synthesis of alpha,beta-disubstituted-alpha-amino acids via direct alkylation of chiral amino acid derivatives with racemic sec-alkyl bromides. Abstracts of Papers American Chemical Society 221(1-2): ORGN 16, 2001

Enantioselective Synthesis of alpha,alpha-Disubstituted Amino Acid Derivatives via Enzymatic Resolution: Preparation of a Thiazolyl-Substituted alpha-Methyl alpha-Benzyl Amine. Journal of Organic Chemistry 61(21): 7398-7401, 1996

Design and synthesis of novel nonpolar host peptides for the determination of the 3-10- and alpha-helix compatibilities of alpha-amino acid building blocks: An assessment of alpha,alpha-disubstituted glycines. Biopolymers 42(5): 575-626, 1997

Powerful chiral phase-transfer catalysts for the asymmetric synthesis of alpha-alkyl- and alpha,alpha-dialkyl-alpha-amino acids. Angewandte Chemie 44(10): 1549-1551, 2005

Lipase-catalyzed kinetic resolution of cyclic trans-1,2-diols bearing a diester moiety: synthetic application to chiral seven-membered-ring alpha,alpha-disubstituted alpha-amino acid. Journal of Organic Chemistry 72(20): 7750-7756, 2007

Asymmetric synthesis of alpha,alpha-disubstituted alpha-amino acid derivatives using MABR promoted rearrangement. Tetrahedron Letters 39(22): 3749-3752, 1998

Efficient synthesis of symmetrical alpha,alpha-disubstituted beta-amino acids and alpha,alpha-disubstituted aldehydes via dialkylation of nucleophilic beta-alanine equivalent. Journal of Organic Chemistry 75(5): 1717-1722, 2010

Synthesis of alpha-amino acids via asymmetric phase transfer-catalyzed alkylation of achiral nickel(II) complexes of glycine-derived Schiff bases. Journal of the American Chemical Society 125(42): 12860-12871, 2003

Combinatorial design of simplified high-performance chiral phase-transfer catalysts for practical asymmetric synthesis of alpha-alkyl- and alpha,alpha-dialkyl-alpha-amino acids. Chemistry An Asian Journal 3(8-9): 1702-1714, 2008

Enantioselective synthesis of alpha-quaternary amino acid derivatives by sequential enzymatic desymmetrization and Curtius rearrangement of alpha,alpha-disubstituted malonate diesters. Journal of Organic Chemistry 75(5): 1612-1619, 2010