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Architecture and function of atropisomeric molecular triads.

Molecular triads, B-A-B, in which the central unit A is aromatic or heteroaromatic, can exist as syn or anti conformers or atropisomers of correspondingly C or S shape. These stereoisomers are either discrete conformer species, often distinguished by NMR spectroscopy, or can be separated at ambient temperature as stable atropisomers. In the latter case syn and anti stereoisomers exhibit different (e.g., complex-forming) properties. Practical applications of atropisomeric triads as ligands in asymmetric dihydroxylation are also discussed.