Selective Nucleophilic Substitution Using Pyrazolate Anions: Easy Approach to Modular Chiral Ligands with Complexing Pyrazole Moieties

• Autorzy: Kowalczyk R. , Skarżewski J.
• Języki publikacji: EN

Abstrakty

EN

A simple method for the stereoselective synthesis of 3,5-disubstituted pyrazolyl alcohols from readily available chiral epoxides is reported. The key step of the synthesis is the ring-opening reation, which occurs by a regio- and enantioselective nucleophilic substitution with pyrazolate anions. An analogous reaction of the pyrazolate anions gave nonracemic (pyrazolyl)oxazolines. Thus obtained modular pyrazole chiral ligands were tested in the Pd-catalyzed Tsuji-Trost and Cu-catalyzed asymmetric cyclopropanation reactions and the enantioselectivities up to 52% ee and 64% ee were at tained in both model reactions, correspondingly.

Słowa kluczowe

EN

chiral ligands; epoxidering opening; asymmetric allylic alkylation; asymmetric cyclopropanation

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2007
• Tom: Vol. 81, nr 11
• Strony: 1987--1999
• Opis fizyczny: Bibliogr. 26 poz., rys.

Twórcy

autor

Kowalczyk R.

autor

Skarżewski J.

• Department of Organic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wyb. Wyspiańskiego 27, 50-370 Wrocław, Poland,

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