Donor Rhodium Carbenes by Retro-Buchner Reaction

Rhodium carbenes are key intermediates in a range of cycloadditions and insertion reactions. Herein, we report the first generation of donor RhII carbenes by decarbenation of 7‐substituted 1,3,5‐cycloheptatrienes. This discovery unlocks an improved retro‐Buchner‐cyclopropanation sequence, a Si−H ins...

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Bibliographic Details
Authors: Mato, Mauro, Echavarren, Antonio M.
Format: article
Status:Versión aceptada para publicación
Publication Date:2018
Country:España
Institution:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repository:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2072/449978
Online Access:http://hdl.handle.net/2072/449978
https://doi.org/10.1002/anie.201813512
Access Level:Open access
Keyword:54
Description
Summary:Rhodium carbenes are key intermediates in a range of cycloadditions and insertion reactions. Herein, we report the first generation of donor RhII carbenes by decarbenation of 7‐substituted 1,3,5‐cycloheptatrienes. This discovery unlocks an improved retro‐Buchner‐cyclopropanation sequence, a Si−H insertion reaction for a broad‐scope synthesis of allylsilanes, and a new method for the vinylogation of aldehydes. The last strategy led to the development of an iterative synthesis of E‐polyenes, and to the total synthesis of navenones B and C.