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

Autor:	Natalie C. Giampietro, John P. Wolfe
Rok vydání:	2008
Předmět:	Allylic strain Stereochemistry Allyl compound Substituent Stereoisomerism General Chemistry Biochemistry Article Catalysis Allyl Compounds Pyrazolidine chemistry.chemical_compound Hydrazines Colloid and Surface Chemistry chemistry Pyrazoles Stereoselectivity Palladium Amination Bond cleavage
Zdroj:	Journal of the American Chemical Society. 130:12907-12911
ISSN:	1520-5126 0002-7863
DOI:	10.1021/ja8050487
Popis:	The stereoselective synthesis of either trans- or cis-3,5-disubstituted pyrazolidines is accomplished via Pd-catalyzed carboamination reactions of unsaturated hydrazine derivatives. The products are obtained in good yield with up to20:1 diastereoselectivity. Stereocontrol is achieved by modulating the degree of allylic strain in the transition state for syn-aminopalladation through a simple modification of the substrate N(2)-substituent. The pyrazolidine products can be further transformed to 3,5-disubstituted pyrazolines via deprotection/oxidation, or to substituted 1,3-diamines via N-N bond cleavage.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::731b5e509ea40ecb57fb377acdc5d775 https://doi.org/10.1021/ja8050487 Zobrazit plný text záznamu