Synthesis of the Quinolizidine Alkaloids (-)-Lasubine II (I) and (.+-.)-Myrtine (II) by Conjugate Addition and Intramolecular Acylation of Amino Esters with Acetylenic Sulfones.

ChemInform ◽  
2005 ◽  
Vol 36 (26) ◽  
Author(s):  
Thomas G. Back ◽  
Michael D. Hamilton ◽  
Vania J. J. Lim ◽  
Masood Parvez
Keyword(s):  
Conjugate Addition ◽  
Quinolizidine Alkaloids ◽  
Amino Esters ◽  
Acetylenic Sulfones

ChemInform Abstract: Syntheses from Chiral Heterocyclic β-Amino Esters. A New Versatile Access to Pyrrolizidine and Quinolizidine Alkaloids.

ChemInform ◽  
2010 ◽  
Vol 32 (44) ◽  
pp. no-no
Author(s):  
Stephane Ledoux ◽  
Elisabeth Marchalant ◽  
Jean-Pierre Celerier ◽  
Gerard Lhommet
Keyword(s):  
Quinolizidine Alkaloids ◽  
Amino Esters

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.

scholarly journals A chiral ligand mediated aza-conjugate addition strategy for the enantioselective synthesis of β-amino esters that contain hydrogenolytically sensitive functionality

Tetrahedron ◽  
2015 ◽  
Vol 71 (46) ◽  
pp. 8838-8847 ◽  
Author(s):  
Robert M. Archer ◽  
Marc Hutchby ◽  
Caroline L. Winn ◽  
John S. Fossey ◽  
Steven D. Bull
Keyword(s):  
Conjugate Addition ◽  
Enantioselective Synthesis ◽  
Chiral Ligand ◽  
Amino Esters

Synthesis ofβ-Amino Esters by the Conjugate Addition of Nitrogen Nucleophiles toα,β-Unsaturated Esters Having Chiralp-Tolylsulfinyl Groups

1997 ◽  
Vol 26 (4) ◽  
pp. 375-376 ◽  
Author(s):  
Haruo Matsuyama ◽  
Nobuhiro Itoh ◽  
Masato Yoshida ◽  
Nobumasa Kamigata ◽  
Sigeru Sasaki ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Unsaturated Esters ◽  
Amino Esters ◽  
Nitrogen Nucleophiles

Conjugate Addition of Amines to Sugar Derived Olefinic Esters: Synthesis of Glycosylated Amino Esters as DNA Topoisomerase-II Inhibitors.

ChemInform ◽  
2003 ◽  
Vol 34 (16) ◽  
Author(s):  
A. R. Khan ◽  
R. P. Tripathi ◽  
V. K. Tiwari ◽  
R. C. Mishra ◽  
V. J. M. Reddy ◽  
...  
Keyword(s):  
Topoisomerase Ii ◽  
Conjugate Addition ◽  
Dna Topoisomerase Ii ◽  
Dna Topoisomerase ◽  
Amino Esters ◽  
Topoisomerase Ii Inhibitors

Syntheses from chiral heterocyclic β-amino esters. A new versatile access to pyrrolizidine and quinolizidine alkaloids

2001 ◽  
Vol 42 (32) ◽  
pp. 5397-5399 ◽  
Author(s):  
Stéphane Ledoux ◽  
Elisabeth Marchalant ◽  
Jean-Pierre Célérier ◽  
Gérard Lhommet
Keyword(s):  
Quinolizidine Alkaloids ◽  
Amino Esters
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