“From Configurational Notation of Stereoisomers to the Conceptual Basis of Stereochemistry” is the title of a lecture [V. Prelog, ACS Symp. Ser. No. 12 (1975) 179] in which the chronologically and alphabetically third member of the CIP-triumvirate discusses the history of the CIP-system. The experience accumulated in the meantime, particularly the efforts to teach computers to use the system as described in 1966 by Cahn, Ingold and Prelog, has shown that certain of its aspects must be more strictly formulated and others modified. Questions dealing with stereoisomers (and stereotopicity), which previously have been treated predominantly in a pragmatic manner, are now discussed in a systematic way.

Basic Principles of the CIP-System and Proposals for a Revision†

The enantioselective synthesis of 3-functionalized oxindole derivatives has experienced an explosive development. This minireview introduces the recent application of rare earth (RE) metal complex catalysts in the synthesis of targeted frameworks. The direct addition reactions of 3-substituted oxindoles or isatins are described, together with a discussion of the catalytic mechanism and related transformations to pharmaceuticals.

Recent progress in enantioselective synthesis of C3-functionalized oxindoles: rare earth metals take action

Amino alcohol effects on the ruthenium(II)-catalysed asymmetric transfer hydrogenation of ketones in propan-2-ol

This review article summarizes the applications of bismuth(III) compounds in organic synthesis since 2002. Although there are an increasing number of reports on applications of bismuth(III) salts in polymerization reactions, and their importance is acknowledged, they are not included in this review. This review is largely organized by the reaction type although some reactions can clearly be placed in multiple sections. While every effort has been made to include all relevant reports in this field, any omission is inadvertent and we apologize in advance for the same (358 references).

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Applications of bismuth(III) compounds in organic synthesis

Publisher Summary The C-nucleosides are a group of C-glycosylated heterocycles in which the anomeric carbon atom is attached to the heterocycle by a C-C bond. C-nucleosides have been mainly from fermentation sources, and have been found to exhibit a variety of interesting biological properties. Pyrazomycin has significant antiviral activity. Formycin, formycin B, and oxazinomycins exhibit, in addition, antitumor activity. The biological importance of most of the naturally occurring C-nucleosides has prompted the exploration of synthetic routes leading to these compounds and their analogs. As synthetic targets, the C-nucleosides have deceptively simple structures, and the design of synthetic routes to them must take two important factors into account. Firstly, the methods selected for C-C bond formation at the anomeric center should be stereocontrolled because the structures known thus far are, with two exceptions, β-D-glycosyl compounds. Secondly, the carbon atom attached to the glycosyl group in a C-nucleoside precursor should be appropriately substituted or be amenable to substitution, so as to allow the elaboration of the other heterocyclic portion of the molecule.

Gloria G. Lyle

Papers

Oxidative Deoximation with Pyridinium Chlorochromate

Rotatory Dispersion Studies. I. Aralkylamines and Alcohols1

Methyl 1-methyl-1,2,3,6-tetrahydroisonicotinate1

Nuclear Magnetic Resonance Study of Oxiranes from Ephedrine Salts1a

Resolution of 2,6-Diphenyl-1-methyl-4-piperidone Oxime, a Novel Example of Molecular Isomerism1,2