Auxiliary controlled 1,3-dipolar cycloadditions of chiral stabilized azomethine ylides

1994 ◽  
Vol 59 (1) ◽  
pp. 4-6 ◽  
Author(s):  
Philip Garner ◽  
Ozdemir Dogan
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloadditions ◽  
Stabilized Azomethine Ylides

1,3-Dipolar Cycloadditions to Unsymmetrical Ketone-Derived Chiral Stabilized Azomethine Ylides: Strategies for the Synthesis of Highly Substituted Amino Acids

Synthesis ◽  
2005 ◽  
pp. 3271-3278 ◽  
Author(s):  
Laurence M. Harwood ◽  
David J. Aldous ◽  
Michael G. Drew ◽  
William N. Draffin ◽  
Estelle M-N. Hamelin ◽  
...  
Keyword(s):  
Amino Acids ◽  
Azomethine Ylides ◽  
Dipolar Cycloadditions ◽  
Stabilized Azomethine Ylides

ChemInform Abstract: Stereocontrolled 1,3-Dipolar Cycloadditions Using Oppolzer′s Camphor Sultam as the Chiral Auxiliary for Carbonyl Stabilized Azomethine Ylides.

ChemInform ◽  
2001 ◽  
Vol 32 (17) ◽  
pp. no-no
Author(s):  
Philip Garner ◽  
Oezdemir Dogan ◽  
Wiley J. Youngs ◽  
Vance O. Kennedy ◽  
John Protasiewicz ◽  
...  
Keyword(s):  
Chiral Auxiliary ◽  
Azomethine Ylides ◽  
Dipolar Cycloadditions ◽  
Stabilized Azomethine Ylides

scholarly journals Synthesis of pyrrolizidines and indolizidines by multicomponent 1,3-dipolar cycloaddition of azomethine ylides

2019 ◽  
Vol 91 (4) ◽  
pp. 575-596 ◽  
Author(s):  
Carmen Nájera ◽  
José Miguel Sansano
Keyword(s):  
Amino Acid ◽  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Amino Acid Derivatives ◽  
Reaction Conditions ◽  
Dipolar Cycloadditions ◽  
Spiro Derivatives ◽  
Stabilized Azomethine Ylides

Abstract Different multicomponent 1,3-dipolar cycloadditions (1,3-DC) of cyclic α-amino acid derivatives with aldehydes and dipolarophiles have been described as efficient and simple methodologies for the synthesis of the pyrrolidine unit of pyrrolizidines and indolizidines. When free cyclic α-amino acids are used, a thermal promoted decarboxylative process generates in situ the corresponding non-stabilized azomethine ylides, which afforded the corresponding pyrrolizidines and indolizidines with a hydrogen in the bicyclic units. This methodology has been employed to the synthesis of complex systems including spiro derivatives when ketones are used as carbonyl component. In addition, working with cyclic α-amino acid derived esters, the three-component 1,3-DC takes place under milder reaction conditions giving the corresponding pyrrolizidines and indolizidines with an alkoxycarbonyl group in the bridge adjacent carbon to the nitrogen. This methodology can be carried out by a double consecutive or stepwise 1,3-DC to provide pyrrolizidines via the precursor prolinates. The conformation of the azomethine ylide controls the endo/exo diastereoselectivity of the 1,3-DC.

Stereocontrolled 1,3-dipolar cycloadditions using Oppolzer's camphor sultam as the chiral auxiliary for carbonyl stabilized azomethine ylides

Tetrahedron ◽  
2001 ◽  
Vol 57 (1) ◽  
pp. 71-85 ◽  
Author(s):  
Philip Garner ◽  
Özdemir Dogan ◽  
Wiley J. Youngs ◽  
Vance O. Kennedy ◽  
John Protasiewicz ◽  
...  
Keyword(s):  
Chiral Auxiliary ◽  
Azomethine Ylides ◽  
Dipolar Cycloadditions ◽  
Stabilized Azomethine Ylides

scholarly journals Influence of N-substituents of carbamoyl-stabilized azomethine ylides in 1,3-dipolar cycloadditions

ARKIVOC ◽  
2002 ◽  
Vol 2001 (2) ◽  
pp. 146-162 ◽  
Author(s):  
Jiří Pospíšil ◽  
Martin Trávníček ◽  
Milan Potáček
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloadditions ◽  
Stabilized Azomethine Ylides
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