Abstract
Abstract Enantiopure five-membered ring nitrones derived from L-tartaric acid and from L-malic acid undergo highly regio- and stereoselective cycloaddition reactions with an excess of racemic 2,3-dihydro-1-phenyl-1H-phospholes producing two readily separable tricyclic cycloadducts and concomitantly effecting kinetic resolution of the dihydrophosphole derivative (diastereomeric ratio up to 10:l; stereoselectivity factor s = kS/kR = 14). The tricyclic cycloadducts feature 2,2′-connection of pyrrolidine and phospholane rings and five to seven contiguous stereogenic centers of which three are induced and one or two are kinetically resolved during the cycloaddition process.
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