Asymmetric N-H Insertion Reaction with Chiral Aminoalcohol as Catalytic Core of Cinchona Alkaloids.
Chem Pharm Bull (Tokyo)
; 67(4): 393-396, 2019.
Article
in En
| MEDLINE
| ID: mdl-30930443
ABSTRACT
In order to develop an efficient organocatalyst for the enantioselective N-H insertion reaction via carbene/carbenoid, the catalytic core of the cinchona alkaloids was investigated. According to our working hypothesis of an eight-membered ring transition state in the N-H insertion reaction, two pairs of enantiomers related to 2-amino-1-phenylethanol were investigated for their chiral inducing potential. Since both (1R,2S)-isomers gave the N-phenyl-1-phenylglycine derivative enriched in the R-form, while their enantiomers gave the S-form, the 2-amino-1-phenylethanol structure is concluded to be the catalytic core of the cinchona alkaloid in the enantioselective N-H insertion reaction via rhodium(II) carbenoid.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Cinchona Alkaloids
/
Amino Alcohols
Language:
En
Journal:
Chem Pharm Bull (Tokyo)
Year:
2019
Type:
Article