A 1,3,2‐Diazaphospholene‐Catalyzed Reductive Claisen Rearrangement

Autor:	Solène Miaskiewicz, Pavel A. Donets, Nicolai Cramer, John H. Reed
Rok vydání:	2019
Předmět:	010405 organic chemistry Chemistry Enantioselective synthesis General Chemistry General Medicine 010402 general chemistry 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences Stereocenter Claisen rearrangement Chemical kinetics
Zdroj:	Europe PubMed Central
ISSN:	1521-3757 0044-8249
DOI:	10.1002/ange.201904411
Popis:	1,3,2-Diazaphospholenes (DAPs) are an emerging class of organic hydrides. In this work, we exploited them as efficient catalysts for very mild reductive Claisen rearrangements. The method is tolerant towards a wide variety of functional groups and operates at ambient temperature. Besides being enantiospecific for substrates with existing stereogenic centers, the diastereoselectivity can be switched by varying solvents and DAP catalysts. The reaction kinetics show direct rearrangements of O-bound phospholene enolates and provide a proof-of-principle for catalytic enantioselective reactions.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::0567d90554ed53beac5989cbadcd994e https://doi.org/10.1002/ange.201904411 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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