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Asymmetric Photochemistry and Photochirogenesis

Griesbeck A.G. (1) and Meierhenrich U.J. (2)

(1) Universität Köln, Institut für Organische Chemie, Greinstraße 4, D-50939 Köln, 
     Germany
(2) Bremen University, Dept. Phys. Chemistry, FB 02, Leobener Straße, 
     D-28359 Bremen, Germany

One of the most interesting phenomena on Earth is the chirality of biomolecules, the origin of which remains unknown. A challenge arising from this phenomenon is the selective, atom-economic synthesis of enantiomerically pure target molecules from nonchiral starting materials. Herein, new developments in the field of asymmetric photochemistry and photochirogenesis are described with special emphasis on absolute asymmetric synthesis. In this context, the elucidation of the ultimate cause of homochirality phenomena on earth and the possible correlation with physicochemical parameters are also presented.

Angewandte Chemie Int. Ed. 41 (2002), 3147-3154
Angewandte Chemie 114 (2002), 3279-3286

This article was cited in: 
Kaneda M, Nishiama Y, Asaoka S: Pressure control of enantiodifferentiating polar addition of
      1,1-diphenylpropene sensitized by chiral naphthalenecarboxylates.
      Organic and Biomolecular Chemistry 2 (2004), 1295-1303.
Saito H, Mori T, Wada T et al.: Diastereoselective [2+2] photocycloaddition of stilbene to chiral
     fumarate. Direct versus charge-transfer excitation. J. Am. Chem. Soc. 126 (2004), 1900-1906.
Perez-Prieto J, Lahoz A, Bosca F et al.: Stereodifferentiation in the decay of triplets and biradicals
     involved in intramolecular hydrogen transfer from phenols or indoles to pi,pi* aromatic ketones.
     J. Org. Chem. 69  (2004), 374-381.
Tsutsumi K, Nakano H, Furutani A et al.: Novel enhancement of diastereoselectivity of [2+2]
     photocycloaddition of chiral cyclohexenones to ethylene by adding naphthalenes
     J. Org. Chem. 69 (2004), 785-789.
Meierhenrich UJ, Thiemann WHP: Photochemical concepts on the origin of biomolecular
      asymmetry. Orig. Life Evol. Biosphere 34 (2004), 111-121.
Pischel U, Abad S, Domingo LR, et al.: Diastereomeric differentiation in the quenching of excited
     states by hydrogen donors. Angew. Chem Int. Edit. 42 (2003), 2531-2534.
Baleizao C, Gigante B, Ribeiro FR, et al.: Photochemistry of chiral pentacoordinated Al salen
     complexes. Chiral recognition in the quenching of photogenerated tetracoordinated Al salen
     transient ba alkenes. Photoch. Photobio. Sci. 2 (2003), 386-392.
Griesbeck AG, Maptue N, Bondock S, et al.: The excimer radiation system: a powerful tool for
     preparative organic photochemistry. A technical note. Photoch. Photobio. Sci. 2 (2003), 450-451 .
Meierhenrich U.J., Munoz Caro G.M., Schutte W.A., Barbier B., Arcones Segovia A., Rosenbauer
     H., Thiemann W.H.-P., Brack A.: The prebiotic synthesis of amino acids - interstellar vs.
     atmospheric mechanisms. European Space Agency ESA Special Publication ESA SP-518 (2002),
     25-30.
Meierhenrich UJ: Comets and earthly life.
      Nachr. Chem. 50 (2002), 1338-1341.
Meierhenrich UJ, Thiemann WHP, Goesmann F, et al.: Enantioselective amino acid analysis in
      cometary matter planned for the Cosac instrument onboard Rosetta lander. In: Lacoste H (ed.)
      Exo-Astrobiologie. ESA SP-518, ISBN: 92-9092-828-X, the Netherlands (2002), p. 477-478.