A new approach to the synthesis of chiral molecules from nonchiral reactants. Asymmetric induction by reaction at one surface of a single (nonchiral) crystal

A Possible Path to the RNA World: Enantioselective and Diastereoselective Purification of Ribose

“…As shown previously, molecules possessing large but realistic dipole moments can be strongly oriented by E of the order of magnitude of several MV/cm (Bielski and Tencer, 2003). D 1 and D 2 may exist naturally, e.g., as an effect of cleavage of some achiral crystals (Chrenchaiah et al 1982;Chrenchaiah et al 1986;Flack 2003) or by design, e.g., through surface modification. Here, only the former case is of interest, as well as the question of a naturally existing E.…”

Life's Single Chirality: Origin of Symmetry Breaking in Biomolecules

“…The enantiotopic faces of crystals have also recently been employed in such a ''geometric'' approach to absolute asymmetric synthesis in a stereoselective reduction reaction by Kuhn [73], acting on similar observations by Holland and Richardson made 20 years earlier [74]. An achiral reactant A ''sees'' only one of the two enantiotopic faces and reacts stereospecifically (Figure 23.11).…”

Concept of Absolute Enantioselective Separation

“…If R = CH 3 the absolute configuration of the dominant enantiomer will be R. After our paper describing the AAS [11] appeared, Professor Kagan [12] pointed to us a related set of papers from the early eighties. Robinson and Holland [13][14][15] published elegant studies in which the mutual orientation of reactants was accomplished by using one surface of an appropriate single (non-chiral) crystal as a chiral template. First, large single crystals of tiglic acid 9 grown from acetone were embedded in an epoxy resin.…”