Transition-Metal-Catalyzed Enantioselective Synthesis of Compounds with Non-Centrochirality

Abstract

Although central chirality based on stereogenic carbon atomsis arguably the most common chiral element in organic chemistry,chiral molecules devoid of stereogenic centers play important rolesin stereoselective organic transformations. In spite of the usefulnessof these CHIRAL COMPOUNDS WITH ‘NON-CENTROCHIRALITY’ inasymmetric synthesis, enantiomerically enriched forms (scalemicforms) of these compounds are primarily obtained by rather classicalmethods. Examples of CATALYTIC enantioselectiveinduction of such non-centrochirality have been extremely rare andthis is thus still a developing area in synthetic organic chemistry.In this review article, transition-metal-catalyzed enantioselectivepreparations of various non-centrochiral compounds, which includecompounds with planar, axial, or helical chirality, are surveyed. 1 Introduction 2 Planar Chirality in Organometallic and Organic Compounds 3 Axial Chirality in Allenes 4 Atropisomeric Axial Chirality in Biaryls 5 Atropisomeric Axial Chirality about Carbon-Nitrogenor Carbon-Carbon Single Bonds in Nonbiaryl Systems 6 Axial Chirality in Spiro Compounds 7 Helical Chirality in ORTHO-FusedPolycyclic Aromatic Compounds 8 Conclusions