Volume 38, Issue 23 pp. 3418-3438
Review

Absolute Asymmetric Synthesis: The Origin, Control, and Amplification of Chirality

Ben L. Feringa

Ben L. Feringa

Department of Organic and Molecular Inorganic Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands, Fax: (+31) 50-3634296

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Richard A. van Delden

Richard A. van Delden

Department of Organic and Molecular Inorganic Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands, Fax: (+31) 50-3634296

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Abstract

Biomolecular homochirality, the origin of which is still a puzzle, has challenged scientists to design chemical systems that provide chiral molecules through absolute asymmetric synthesis and to amplify a small stereochemical bias in such systems. The photoresolution of the enantiomers of helical-shaped, sterically overcrowded alkene 1 with circularly polarized light and the transduction of the stereochemical information by triggering the helical arrangement of a large collection of achiral molecules in a twisted nematic liquid crystalline phase (2) are examples of control and amplification of chirality.

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