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Cover Picture: (Adv. Synth. Catal. 8/2013)
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201390014
Subject(s) - chemistry , substrate (aquarium) , catalysis , enantioselective synthesis , stereocenter , hydrogen , microwave , asymmetric hydrogenation , organic chemistry , medicinal chemistry , combinatorial chemistry , oceanography , physics , quantum mechanics , geology
The front cover picture, provided by Maurizio Taddei, Marcello Rasparini and coauthors, illustrates the asymmetric hydrogenation of E‐ enol acetates to β‐acetoxy carboxylic acids and subsequently to β‐hydroxy acids. These novel hydrogenation substrates, reduced under the catalysis of a [Rh( S )‐Phanephos(cod)]complex, are prepared from racemic substituted β‐keto esters. The catalyst‐substrate interaction is so strong that hydrogenation can be successfully accelerated using microwave dielectric heating, allowing decrease of the hydrogen pressure while maintainingees in excess of 95%. These results conclusively confirm that it is possible to carry out enantioselective synthesis in microwave ovens. The presence of stereocenters and large substituents on the substrate does not interfere with the enantioselectivty of hydrogenation. The process, scaled up to 6 g of substrate using microwaves and to larger quantities using standard autoclaves (under 30 bar of hydrogen), was applied to the production of Aliskiren (Novartis), the first direct renin inhibitor which is used as a treatment for hypertension. Details of this work can be found in the communication by Taddei, Rasparini and co‐authors on pages 1449–1454 (DOI:10.1002/adsc.201200934) .