Asymmetric 1,3-dipolar cycloaddition reactions between enals and nitrones catalysed by half-sandwich rhodium or iridium diphosphane complexes

The aqua complexes ¿(¿5-C5Me5)M¿PP*)¿H2O)]¿SbF6]2 (M = Rh, Ir; PP* = chiral diphosphane) have been tested as catalysts for the asymmetric 1,3-dipolar cycloaddition of nitrones to a,ß-unsaturated aldehydes. Quantitative conversions with very high regioselectivity, perfect endo selectivity and excellent enantioselectivity (up to 99% ee) were achieved. The stereochemical outcome was analyzed on the basis of the stereoelectronic properties of the intermediate enal complexes of the formula ¿(¿5-C5Me5)M¿PP*)¿enal)]¿SbF6]2