This page lists useful sources of further information which
were published too late to be included in the supplementary reading sections of
the main text.
E.M. Geertsema, A. Meetsma, and B.L. Feringa ‘Asymmetric Synthesis of Overcrowded Alkenes by Transfer of Axial Single Bond Chirality to Axial Double Bond Chirality’ Angew. Chem., Int. Ed. Engl. 1999, 38, 2738. A synthesis of an unusual class of alkenes which exhibit enantiomerism rather than cis-trans isomerism due to the substituents on the alkene being non-coplanar.
M. Avalos, R. Babiano, P. Cintas, J.L. Jimenez, and J.C. Palacios 'Absolute Asymmetric Synthesis under Physical Fields: Facts and Fictions' Chemical Reviews, 1998, 98, 2391-404. A review of the ways in which circularly polarized light and other non-symmetric physical influences could result in the formation of a non-racemic, chiral product from achiral starting materials.
B.L. Feringa, and R.A. van Delden ‘Absolute Asymmetric Synthesis: The Origin, Control, and Amplification of Chirality’ Angew. Chem., Int. Ed. Engl. 1999, 38, 3418. A review of the ways in which homochiral natural products could have been formed.
Y. Inoue, T. Wada, S. Asaoka, H. Sato, and J.-P. Pete ‘Photochirogenesis: multidimensional control of asymmetric photochemistry’ Chem. Commun. 2000, 251. A review of asymmetric induction using circularly polarized light.
J. Podlech 'New Insight into the Source of Biomolecular Homochirality: An Extraterrestrial Origin for Molecules of Life' Angew. Chem., Int. Ed. Engl. 1999, 38, 477. A short discussion of a way in which non-racemic amino acids could be formed in space.
H. Buschmann, R. Thede, and D. Heller ‘New Developments in the Origins of the Homochirality of Biologically Relevant Molecules’ Angew. Chem., Int. Ed. Engl. 2000, 39, 4033. A discussion of the possible role of parity violation by the electroweak interaction and asymmetric amplification in determining the absolute configuration of natural products.
T. Wirth 'Chiral selenium compounds in organic synthesis' Tetrahedron, 1999, 55, 1. A review of the synthesis and applications of chiral selenium compounds. In some cases the selenium atom is a stereocentre, in other a stereofeature is present elsewhere in the molecule.
B. Thertien and T.R. Ward 'Synthesis of a Configurationally Stable Three-Legged Piano-Stool Complex' Angew. Chem., Int. Ed. Engl. 1999, 38, 405. The synthesis of an enantiomerically pure (arene)RuXYZ complex in which X and Y are also connected to the aryl group.
U. Knof, and A. von Zelewsky 'Predetermined Chirality at Metal Centres' Angew. Chem., Int. Ed. Engl. 1999, 38, 302. A review of the synthesis and structure of metal complexes bearing chiral ligands in which the metal atom(s) is also a stereocentre. Also included are helical metal complexes.
H. Brunner 'Optically Active Organometallic Compounds of Transition Elements with Chiral Metal Atoms' Angew. Chem., Int. Ed. Engl. 1999, 38, 1194. Another review of the synthesis and structure of metal complexes bearing chiral ligands in which the metal atom(s) is also a stereocentre.
E.M. Geertsema, A. Meetsma, and B.L. Feringa ‘Asymmetric Synthesis of Overcrowded Alkenes by Transfer of Axial Single Bond Chirality to Axial Double Bond Chirality’ Angew. Chem., Int. Ed. Engl. 1999, 38, 2738. A synthesis of an unusual class of alkenes which exhibit enantiomerism rather than cis-trans isomerism due to the substituents on the alkene being non-coplanar.
A. de Meijere, A.F. Khlebnikov, R.R. Kostikov, S.I. Kozhushkov, P.R. Schreiner, A. Wittkopp, and D.S. Yufit ‘The First Enantiomerically Pure Triangulane (M)-Trispiro[2.0.0.2.1.1]nonane Is a s-[4]Helicene’ Angew. Chem., Int. Ed. Engl. 1999, 38, 3474. The synthesis of a novel example of an enantiomerically pure helical molecule.
D. Gao, S. Schefzick, and K.B. Lipkowitz ‘Relationship between Chirality Content and Stereoinduction: Identification of a Chiraphore’ J. Am. Chem. Soc. 1999, 121, 9481. An attempt to quantify the chirality of a molecule and its relationship to asymmetric induction.
S. Allenmark and V. Schurig 'Chromatography on chiral stationary phases', J. Mater. Chem. 1997, 7, 1955-63. A review of the use of chiral chromatography to separate enantiomers.
R. Tamura, H. Takahashi, K. Hirotsu, Y. Nakajima, T. Ushio, and F. Toda 'Unusual Disordered Crystal Structure of a racemate Exhibiting a Novel Enantiomeric Resolution: Preferential Enrichment', Angew. Chem., Int. Ed. Engl. 1998, 37, 2876-8. This paper describes the rare circumstances where one enantiomer of a racemate can crystallize selectively without the need to seed the solution with crystals of one of the enantiomers.
T. Vries, H. Wynberg, E. van Echten, J. Koek, W. ten Hoeve, R.M. Kellogg, Q.B. Broxtermann, A. Minnaard, B. Kaptein, S. van der Sluis, L. Hulshof, and J. Kooistra ' The Family Approach to the Resolution of Racemates', Angew. Chem., Int. Ed. Engl. 1998, 37, 2849-54. A description of a methodology for resolution which uses mixtures of enantiomerically pure compounds as resolving agents rather than a single enantiomerically pure compound. For a subsequent article which provides a critical discussion of this work see: A. Collet 'Resolution of Racemates: Did You say ''Classical''?', Angew. Chem., Int. Ed. Engl. 1998, 37, 3239-41.
U.T. Strauss, U. Felfer, and K. Faber 'Biocatalytic transformation of racemates into chiral building blocks in 100% chemical yield and 100% enantiomeric excess', Tetrahedron: Asymmetry 1999, 10, 107. A review of the ways in which enzymatic resolutions can be used to give >50% yields in resolutions.
D.K. Kondepudi, J. Laudadio, and K. Asakura 'Chiral Symmetry Breaking in Stirred Crystallization of 1,1'-Binaphthyl Melt', J. Am. Chem. Soc.1999, 121, 1448-51. A description of the spontaneous resolution of 1,1'-binaphthyl during crystallization of a stirred melt.
J. Eames ‘Parallel Kinetic Resolutions’, Angew. Chem., Int. Ed. Engl. 2000, 39, 885-888. A discussion of a method which can occasionally be used to increase the efficiency of a kinetic resolution.
E. Vedejs, R.W. Chapman, S. Lin, M. Muller, and D.R. Powell ‘Crystallization-Induced Asymmetric Transformation vs Quasi-Racemate Formation in Tetravalent Boron Complexes’, J. Am. Chem. Soc. 2000, 122, 3047-3052. A description of epimerization during crystallization leading to the conversion of a mixture of diastereomers to a single stereoisomer during crystallization.
O. Tissot, M. Gouygou, F. Dallemer, J-C. Daran, and G.G.A. Balavoine ‘The
Combination of Spontaneous Resolution and Asymmetric Catalysis: A Model for the
Generation of Optical Activity from a Fully Racemic System’, Angew. Chem.,
Int. Ed. Engl. 2001, 40, 1076-8. An example of
conglomerate crystallization, being used to form enantiomerically pure chiral
ligands which could then be complexed to a metal to give a configurationally
stable and catalytically active complex.
C. Girard and H.B. Kagan 'Nonlinear Effects in Asymmetric Synthesis and Stereoselective
Reactions: Ten Years of Investigation', Angew. Chem., Int. Ed. Engl. 1998,
37, 2922-59. A review of non-linear effects in asymmetric
catalysis.
B.L. Feringa, and R.A. van Delden ‘Absolute Asymmetric Synthesis: The Origin, Control, and Amplification of Chirality’ Angew. Chem., Int. Ed. Engl. 1999, 38, 3418. A review of the ways in which homochiral natural products could have been formed, including the use of non-linear catalysis to enhance initially very small enantiomeric excesses.
D. Gao, S. Schefzick, and K.B. Lipkowitz ‘Relationship between Chirality Content and Stereoinduction: Identification of a Chiraphore’ J. Am. Chem. Soc. 1999, 121, 9481. An attempt to quantify the chirality of a molecule and its relationship to asymmetric induction.