The products of the condensation reactions of twenty-six different 1,2-amino alcohols with excess aqueous formaldehyde were identified, with the help of a simple and effective analytical technique based on mass spectroscopy. With a few exceptions, which arise from steric or solubility effects, most amino alcohols form bis(oxazolidine)methane adducts preferentially.

(S)-4-Oxopipecolic acid has been prepared in enantiomerically pure form from two readily accessible starting materials, (R)-N-(cyanomethyl)-4-phenyloxazolidine (2) and 2(methoxymethoxy)allyl chloride, (3, MOM-allyl chloride). This strategy exploits the complementary electrophile/nucleophile reactivity at each end of this pair of 3-atom unit building blocks. Thus, alkylation of the anion of 2 with 3 (creation of the piperidine C-2-C-3 bond) followed by Lewis acid induced cyclisation (creation of the C-5-C-6 bond), leads principally to a bicyclic intermediate 5 which incorporates a protected form of the title compound. Subsequent chemical transformations lead to the target molecule in an overall yield of 20% for the five-step sequence. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

The title compound was prepared in two diastereomeric forms and cyclised efficiently with boron trifluoride to give three stereoisomers of a hetero-bicyclic structure; the stereochemical profile of the reaction is explained in terms of configuration-dependent conformational preferences.

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The isolation of isoindoline 4 by oxidative trapping indicates that a tricyclic η5 complex is a contributing form of the anion derived from the title compound 3.

The palladium-catalyzed addition of amines to allenes in the presence of triethylammonium iodide leads to allylic amines.

The palladium and base-catalyzed addition of malonates and acetylacetates to allenic hydrocarbons affords allylated dicarbonyl compounds. Results account likely for an unprecedented hydropalladation process of the allenic unit which leads to a π-allylpalladium intermediate.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

The palladium-catalysed reaction of vinyl halides with the anions of 1,1-dimethyl-2,3-butadienylmalonates leads to 4-dienyl γ-lactones through an unexpected alkylative O-cyclisation pathway due to the steric demand of the α-allenic gem-dimethyl group.