Stereoselective synthesis of?-amino acids via conjugate addition of nitrogen nucleophiles to?,?-unsaturated esters ? Recent advances

Amino Acids ◽  
1996 ◽  
Vol 11 (3-4) ◽  
pp. 397-408 ◽  
Author(s):  
N. Sewald
Keyword(s):  
Amino Acids ◽  
Stereoselective Synthesis ◽  
Conjugate Addition ◽  
Unsaturated Esters ◽  
Recent Advances ◽  
Nitrogen Nucleophiles

Recent Advances in Stereoselective Synthesis and Application of β-Amino Acids

2009 ◽  
Vol 41 (6) ◽  
pp. 429-478 ◽  
Author(s):  
Brad E. Sleebs ◽  
T. T. Van Nguyen ◽  
Andrew B. Hughes
Keyword(s):  
Amino Acids ◽  
Stereoselective Synthesis ◽  
Recent Advances

scholarly journals Stereoselective synthesis of perillaldehyde-based chiral β-amino acid derivatives through conjugate addition of lithium amides

2014 ◽  
Vol 10 ◽  
pp. 2738-2742 ◽  
Author(s):  
Zsolt Szakonyi ◽  
Reijo Sillanpää ◽  
Ferenc Fülöp
Keyword(s):  
Amino Acids ◽  
Stereoselective Synthesis ◽  
Minor Component ◽  
Conjugate Addition ◽  
Building Blocks ◽  
Major Product ◽  
Amino Ester ◽  
Chiral Amine ◽  
Amino Esters ◽  
Lithium Amides

The Michael addition of dibenzylamine to (+)-tert-butyl perillate (3) and to (+)-tert-butyl phellandrate (6), derived from (S)-(−)-perillaldehyde (1), resulted in diastereomeric β-amino esters 7A–D in a moderately stereospecific reaction in a ratio of 76:17:6:1. After separation of the diastereoisomers, the major product, cis isomer 7A, was quantitatively isomerized to the minor component, trans-amino ester 7D. All four isomers were transformed to the corresponding β-amino acids 10A–D, which are promising building blocks for the synthesis of β-peptides and 1,3-heterocycles in three steps. The steric effects of the isopropyl group at position 4 and of the α-methyl substituent of (R)-N-benzyl-N-α-methylbenzylamine on the reactivity were also studied and, upon application of a chiral amine, excellent stereoselectivity of the conjugate addition was observed. Amino ester 11 was obtained as a single product and transformed to the corresponding amino acids 10A and 10D in good yields on the gram scale.

Stereoselective synthesis of pinane-based β- and γ-amino acids via conjugate addition of lithium amides and nitromethane

2010 ◽  
Vol 21 (20) ◽  
pp. 2498-2504 ◽  
Author(s):  
Zsolt Szakonyi ◽  
Árpád Balázs ◽  
Tamás A. Martinek ◽  
Ferenc Fülöp
Keyword(s):  
Amino Acids ◽  
Stereoselective Synthesis ◽  
Conjugate Addition ◽  
Lithium Amides

Phase-transfer catalysis and the ion pair concept

2020 ◽  
Vol 0 (0) ◽  
Author(s):  
Florenci V. González Adelantado
Keyword(s):  
Amino Acids ◽  
Phase Transfer Catalysis ◽  
Phase Transfer ◽  
Conjugate Addition ◽  
Ion Pair ◽  
Asymmetric Reactions ◽  
Conjugate Additions ◽  
Mannich Reactions ◽  
Recent Advances

AbstractThis review outlines the recent advances in the field of asymmetric phase-transfer catalysis and the ion-pair concept including alkylation of amino acids and peptides, oxyindoles and other substrates, conjugate additions, fluorinations, photo-induced phase-transfer catalysis, Nitro-Mannich reactions, heterocyclizations and cycloadditions for the preparation of heterocycles, derivatization of isoxazoles, umpolung conjugate addition of imines and other three asymmetric reactions.

ChemInform Abstract: Recent Advances in Stereoselective Synthesis and Application of β-Amino Acids

ChemInform ◽  
2010 ◽  
Vol 41 (12) ◽  
Author(s):  
Brad E. Sleebs ◽  
T. T. Van Nguyen ◽  
Andrew B. Hughes
Keyword(s):  
Amino Acids ◽  
Stereoselective Synthesis ◽  
Recent Advances

Recent advances in the stereoselective synthesis of β-amino acids

Tetrahedron ◽  
2002 ◽  
Vol 58 (40) ◽  
pp. 7991-8035 ◽  
Author(s):  
Mei Liu ◽  
Mukund P. Sibi
Keyword(s):  
Amino Acids ◽  
Stereoselective Synthesis ◽  
Recent Advances

Progress in recent development of stereoselective synthesis of β2-amino acid derivatives from β-nitroacrylate derivatives

2020 ◽  
Vol 18 (16) ◽  
pp. 2991-3006
Author(s):  
Hao-Wei Zeng ◽  
Ping-Yu Wu ◽  
Hsyueh-Liang Wu
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Stereoselective Synthesis ◽  
Amino Acid Derivatives ◽  
Recent Advances

β2-Amino acids: recent advances in the synthesis of β2-amino acids and their derivatives from various stereoselective transformations of β-nitroacrylates are summarized.

Sign in / Sign up

Export Citation Format

Share Document