Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 69, Issue 13, Pages 4412-4428Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo049773m
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A full account of the development of the first catalytic manifold for the additions of allylboronates to aldehydes is described. The thermal additions (both diastereospecific and enantioselective) of 2-carboxyester 3,3-disubstituted allylboronates 1 to both aromatic and aliphatic aldehydes give biologically and synthetically important exo-methylene butyrolactones 2 containing a beta-quaternary carbon center. Although the thermal reaction requires 14 d at room temperature to reach completion, the presence of certain metal salts allows for a 12-16 h reaction while preserving the diastereospecificity observed in the uncatalyzed process. Preliminary mechanistic studies on the origin of the catalytic effect are described as well as stereoselective transformations of lactones 2 into cyclic and acyclic stereotriads with potential usefulness as synthetic intermediates.
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