Synthesis and characterization of homochiral cholesteryl 1-alkenesulfinate esters

Autor: Adrian L. Schwan, Rick R. Strickler
Rok vydání: 2000
Předmět:
Zdroj: Tetrahedron: Asymmetry. 11:4843-4852
ISSN: 0957-4166
Popis: A number of α,β-unsaturated sulfinyl chlorides 1 has been separately prepared and treated with (−)-cholesterol under various conditions some of which incorporated chiral amines quinine or quinidine. Some ( R S ) vinylic sulfinates could be isolated in enantiopure form following one or two recrystallizations of the resulting diastereomeric mixtures of (−)-cholesteryl 1-alkenesulfinates 2 . Access to diastereomerically enriched ( S S ) vinylic sulfinates (66–75% de) was achieved in three instances. Absolute stereochemical assignments were made with the assistance of the chiral solvating agent ( R )-2,2,2-trifluoro-1-(9-anthryl)ethanol.
Databáze: OpenAIRE