Asymmetric Domino Aza-Michael Addition/[3+2] Cycloaddition Reactions as a Versatile Approach to alpha,beta,gamma,-Triamino Acid Derivatives

0427700 - ÚOCHB 2015 RIV US eng J - Článek v odborném periodiku
Kapras, Vojtěch - Pohl, Radek - Císařová, I. - Jahn, Ullrich
Asymmetric Domino Aza-Michael Addition/[3+2] Cycloaddition Reactions as a Versatile Approach to alpha,beta,gamma,-Triamino Acid Derivatives.
Organic Letters. Roč. 16, č. 4 (2014), s. 1088-1091. ISSN 1523-7060. E-ISSN 1523-7052
Institucionální podpora: RVO:61388963
Klíčová slova: 1,3-dipolar cycloaddition * lithium amides * aza-Michael addition * amino acids * pyrazoles
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 6.364, rok: 2014

Nonproteinogenic amino acids are prepared by an unprecedented domino aza-Michael addition-1,3-dipolar cycloaddition, leading to enantiopure highly substituted pyrrolidinopyrazolines. Nonaflyl azide serves as highly effective diazo transfer reagent, forming the link between the conjugate addition and cycloaddition steps. The resulting pyrrolidinopyrazolines can be rapidly transformed to either alpha,beta,gamma-triamino acids or 3,4-methano-beta-prolines. Peptide coupling can be regioselectively conducted at each of the amino groups.
Trvalý link: http://hdl.handle.net/11104/0233202