End-Group-Differentiating Ozonolysis of Norbornene Systems to Afford Access to Highly Substituted Cyclopentane Rings

SEBASTIÁN A. TESTERO; MARÍA I. MANGIONE; ALEJANDRA G. SUÁREZ; ROLANDO A. SPANEVELLO

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

WILEY-V C H VERLAG GMBH

Lugar: Weinheim; Año: 2013 p. 5236 - 5245

1434-193X

The end-group-differentiating ozonolysis concept is discussed, with an emphasis on norbornene systems. Different remote functional groups in endo positions in norbornene derivatives are able to direct the primary ozonide fragmentation. By analysis of the factors affecting the regioselectivity, a rule to predict the direction of the primary ozonide rupture 11 is formulated. These reactions give access to highly substituted cyclopentane rings and provide opportunities for their subsequent regioselective manipulation.