Catalytic enantioselective Amadori–Heyns rearrangement of racemic α-hydroxy ketones with arylamines: synthesis of optically active α-arylamino ketones

2013 ◽  
Vol 49 (78) ◽  
pp. 8812 ◽  
Author(s):  
Angelo Frongia ◽  
Francesco Secci ◽  
Francesca Capitta ◽  
Pier Paolo Piras ◽  
Maria Luisa Sanna
Keyword(s):  
Optically Active ◽  
Hydroxy Ketones

ChemInform Abstract: Catalytic Enantioselective Amadori-Heyns Rearrangement of Racemic α-Hydroxy Ketones with Arylamines: Synthesis of Optically Active α-Arylamino Ketones.

ChemInform ◽  
2014 ◽  
Vol 45 (5) ◽  
pp. no-no
Author(s):  
Angelo Frongia ◽  
Francesco Secci ◽  
Francesca Capitta ◽  
Pier Paolo Piras ◽  
Maria Luisa Sanna
Keyword(s):  
Optically Active ◽  
Hydroxy Ketones

Synthesis and Characterisation of Bridged Morpholine Derivatives Fused to a Phenanthrene Ring System

2017 ◽  
Vol 41 (4) ◽  
pp. 210-215 ◽  
Author(s):  
H. Surya Prakash Rao ◽  
Satish Vijjapu
Keyword(s):  
Spectral Analysis ◽  
Ring System ◽  
Optically Active ◽  
Theoretical Studies ◽  
Stereoselective Reduction ◽  
Steric Interactions ◽  
Conformationally Restricted ◽  
Hydroxy Ketones ◽  
Morpholine Derivatives

The synthesis of conformationally restricted and facially biased bridged morpholine derivatives fused to a phenanthrene ring system was prepared in a three-step sequence involving: (i) Voight rearrangement; (ii) stereoselective reduction of ketone and (iii) iodine mediated cyclisation, the α-allyl-α-hydroxy-ketones gave the corresponding bridged N-substituted morpholines. One of the bridged morpholine derivatives fused to a phenanthrene ring system was optically active. The NMR spectral analysis and theoretical studies show that substitution on nitrogen prefers exo-orientation, possibly to avoid steric interactions with the phenanthrene moiety.

Applications of Optically Active Aryl Cyanohydrins in the Synthesis of α-Hydroxy Aldehydes, α-Hydroxy Ketones and β-Hydroxy Amines

1990 ◽  
Vol 43 (12) ◽  
pp. 2045 ◽  
Author(s):  
WR Jackson ◽  
HA Jacobs ◽  
GS Jayatilake ◽  
BR Matthews ◽  
KG Watson
Keyword(s):  
Optical Purity ◽  
Optically Active ◽  
Aryl Aldehydes ◽  
High Optical Purity ◽  
Hydroxy Ketones ◽  
Hydroxy Aldehydes

Cyanohydrins, prepared in high optical purity from aryl aldehydes, have been converted into α- hydroxy aldehydes, β- hydroxy ketones and β- hydroxy amines without any racemization and frequently with good stereoselectivity for the erythro-diastereoisomer (>90%) at the newly introduced stereogenic centre.

Sign in / Sign up

Export Citation Format

Share Document