Base treatment of hydrazonoyl chloride 2 with MeOPEG-supported acrylates 1 and acrylamides 5 gave the corresponding MeOPEG-supported 4,5-dihydropyrazoles 3 and 6. Basic hydrolysis of the cycloadducts caused the removal of the MeOPEG pendant giving 5-carboxy- or 5-aminocarbonyl- 4,5-dihydropyrazoles 7 and 8, respectively. Cycloaddition between 2 and enantiopure MeOPEG-supported acrylamide 10 gave a mixture of MeOPEG-supported cycloadducts 11 and 12 with low diastereoselectivity.
Nitrilimine cycloadditions to MeOPEG-bounded alkenyl dipolarophiles / L. Garanti, G. Molteni, P. Casati. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. 1. - ISSN 1472-7781. - 2:22(2002), pp. 2504-2508.
Nitrilimine cycloadditions to MeOPEG-bounded alkenyl dipolarophiles
G. Molteni;
2002
Abstract
Base treatment of hydrazonoyl chloride 2 with MeOPEG-supported acrylates 1 and acrylamides 5 gave the corresponding MeOPEG-supported 4,5-dihydropyrazoles 3 and 6. Basic hydrolysis of the cycloadducts caused the removal of the MeOPEG pendant giving 5-carboxy- or 5-aminocarbonyl- 4,5-dihydropyrazoles 7 and 8, respectively. Cycloaddition between 2 and enantiopure MeOPEG-supported acrylamide 10 gave a mixture of MeOPEG-supported cycloadducts 11 and 12 with low diastereoselectivity.
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