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Enantioselective Access to Robinson Annulation Products and Michael Adducts as Precursors
Author(s) -
Gallier Florian,
Martel Arnaud,
Dujardin Gilles
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201701401
Subject(s) - annulation , enantioselective synthesis , chemistry , michael reaction , enantiomer , adduct , conjugate , aldol reaction , derivative (finance) , stereochemistry , organic chemistry , combinatorial chemistry , catalysis , mathematics , business , mathematical analysis , finance
The Robinson annulation is a reaction that has been useful for numerous syntheses since its discovery in 1935, especially in the field of steroid synthesis. The products are usually obtained after three consecutive steps: the formation of an enolate (or derivative), a conjugate addition, and an aldol reaction. Over the years, several methodological improvements have been made for each individual step or alternative routes have been devised to access the Robinson annulation products. The first part of this Review outlines the most relevant developments towards the formation of monocarbonyl‐derived Robinson annulation products (MRA products, MRAPs) and activated monocarbonyl‐derived Robinson annulation products (AMRA products, AMRAPs). The following sections are then devoted to the diastereoselective and enantioselective synthesis of these products, while the last section describes the enantiomeric resolution of racemic mixtures.