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Free Radical Addition and Cyclization Reactions of [2-(4-(S)-Isopropyl-2-oxazoline)-5-phenyl]dialkyltin Hydrides

Stępień A., Petrosyan A., Wilk M., Cmoch P., Rupnicki L., Staliński K.

Polish Journal of Chemistry

2005

Vol. 79 / nr 6

1015-1024

Radical addition reactions of [2-(4-(S)-isopropyl-2-oxazoline)-5-phenyl]dibutyl and dimethyl hydrides to activated double/triple bonds took place in good yields. Triethylborane in presence of oxygen can serve as a radical initiator. Addition of stannyl radicals to N,N-(2-methoxycarbonyl-allyl)benzyl glycinate results in formation of the corresponding piperidine derivatives. The intramolecular tandem radical addition/ cyclization process can be performed in high yields and good diastereoselectivity.