Science of Synthesis

Lu, S. -M.; Zhou, Y. -G., Science of Synthesis: Stereoselective Synthesis, (2011) 1, 257.

General Introduction

The asymmetric hydrogenation of aromatic and heteroaromatic compounds is a useful reaction as it provides a convenient access to numerous saturated or partially saturated chiral cyclic compounds. However, this powerful method has been developed quite recently and it is much less explored than the hydrogenation of traditional substrates such as ketones, imines, and alkenes.[‌1‌–‌7‌] One of the most important reasons for this is the inherent aromatic stabilization of the starting materials. Thus, reduction of one or more aromatic double bonds is commonly accompanied by partial or total loss of aromatic stabilization;[‌8‌] this reduction in resonance energy remains a formidable issue for the successful asymmetric hydrogenation of arenes and hetarenes. Nevertheless, asymmetric hydrogenation of aromatic and heteroaromatic compounds provides a straightforward and efficient route to enantioenriched chiral cyclic compounds. The search for efficient catalyst systems for the asymmetric hydrogenation of multi-unsaturated substrates continues and much effort has already been expended in this area, especially since the beginning of the 21st century. A number of specific reviews have been published, including those by Glorius,[‌9‌] Kuwano,[‌10‌] and Zhou[‌11‌,‌12‌] and, as a result, this account summarizes the progress achieved in a broader area; heterogeneous asymmetric hydrogenation of aromatic and heteroaromatic compounds will not be discussed here in detail.

References