Practical Large-Scale Synthesis of 3,4-Isopropylidenedioxypyrrolidine Hydrotosylate: Atom Economical Self-Hydrogenolysis of a Crystalline Borane−Benzylamine Adduct

Autor:	Steven J. Brenek, Busch Frank R, Michel Couturier, Joanna Teresa Negri, John L. Tucker, Brian M. Andresen, David J. am Ende, Jeffrey B. Jorgensen, Pascal Dube
Rok vydání:	2001
Předmět:	Tandem Organic Chemistry Borane Cleavage (embryo) Combinatorial chemistry Adduct chemistry.chemical_compound Benzylamine chemistry Hydrogenolysis Atom Organic chemistry Protonolysis Physical and Theoretical Chemistry
Zdroj:	Organic Process Research & Development. 6:42-48
ISSN:	1520-586X 1083-6160
DOI:	10.1021/op0102161
Popis:	An efficient four-step sequence has been developed for the synthesis of 3,4-isopropylidenedioxypyrrolidine hydrotosylate starting from inexpensive N-benzylmaleimide. This approach features a novel N-debenzylation procedure that utilizes the corresponding borane−benzylamine complex as an internal hydrogen-transfer source. This palladium-catalyzed tandem protonolysis/hydrogenolysis allows cleavage of the borane−amine adduct and debenzylation in a single operation.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::17e8dd5678cc3cf5db9deddcd815c495 https://doi.org/10.1021/op0102161 Zobrazit plný text záznamu