Pyrrole-Protected ß-Aminoalkylzinc Reagents for the Enantioselective Synthesis of Amino-Derivatives.
Chemistry
; 26(41): 8951-8957, 2020 Jul 22.
Article
em En
| MEDLINE
| ID: mdl-32196786
ABSTRACT
Chiral ß-aminoalkylzinc halides were prepared starting from optically pure commercial ß-amino-alcohols. These amino-alcohols were converted to the corresponding N-pyrrolyl-protected alkyl iodides which undergo a zinc insertion in the presence of LiCl (THF, 25 °C, 10-90â
min). Subsequent Negishi cross-coupling or acylation reactions with acid chlorides produced amino-derivatives with retention of chirality. Diastereoselective CBS-reductions of some prepared N-pyrrolyl-ketones provided 1,3-subsituted N-pyrrolyl-alcohols with high diastereoselectivity. Additionally, a deprotection procedure involving an ozonolysis allowed the conversion of the pyrrole-ring into a formamide without loss of optical purity.
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Base de dados:
MEDLINE
Idioma:
En
Ano de publicação:
2020
Tipo de documento:
Article
País de afiliação:
Alemanha