Intranet

ICIQ research selected by the Editorial Board of Synfacts

Melchiorre‘s and Urakawa‘s paper published in JACS, the one that was highlighted by the Editors of Science, has also been selected byt the Editorial Board of Synfacts.

Diastereodivergent Asymmetric Sulfa-Michael Additions of α-Branched Enones using a Single Chiral Organic Catalyst

Xu Tian, Carlo Cassani, Yankai Liu, Antonio Moran, Atsushi Urakawa, Patrizia Galzerano, Elena Arceo, and Paolo Melchiorre*

J. Am. Chem. Soc., 2011, 133 (44), pp 17934–17941

‘In this research, we have found a way of modulating the diastereoselectivity of a single catalyst using a proper chemical signal, to select “at will” which one among the full matrix of stereoisomers is selectively formed (control over the relative and absolute configuration).’ – says Professor Melchiorre.

In the paper they explain how simple modifications to the reaction conditions of the sulfa-Michael reaction of α,β-disubstituted unsaturated ketones can switch the diastereoselectivity of a single chiral catalyst to obtain either the syn or anti product with high enantioselectivity.

‘I am excited with the idea that engineering a chiral catalyst whose catalysis function changes in response to an external chemical stimulus may become a key design and a conceptual framework for designing future generations of chiral catalysts, expanding the way chemists think about making chiral molecules.’ – adds Paolo.