Stereoselective Synthesis of cis- or trans-3,5-Disubstituted Pyrazolidines via Pd-Catalyzed Carboamination Reactions: Use of Allylic Strain to Control Product Stereochemistry Through N-Substituent Manipulation
作者： Natalie C. Giampietro , John P. Wolfe
DOI: 10.1021/JA8050487
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摘要: The stereoselective synthesis of either trans- or cis-3,5-disubstituted pyrazolidines is accomplished via Pd-catalyzed carboamination reactions unsaturated hydrazine derivatives. products are obtained in good yield with up to >20:1 diastereoselectivity. Stereocontrol achieved by modulating the degree allylic strain transition state for syn-aminopalladation through a simple modification substrate N2-substituent. pyrazolidine can be further transformed 3,5-disubstituted pyrazolines deprotection/oxidation, substituted 1,3-diamines N−N bond cleavage.
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