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Diastereofacial solid phase synthesis and self-promoted cleavage of a [2.2.1] bicyclic diversity scaffold.

PMID: 11975593 (view PubMed database entry)
DOI: 10.1021/ol017264q (read at publisher's website )

Sergey N Savinov, David J Austin,

[reaction: see text]. We have previously described a diastereofacially selective 1,3-dipolar cycloaddition reaction of isom√ľnchnones with vinyl ethers. While adapting this methodology for solid phase synthesis, we discovered a chemoselective and self-promoted linker aminolysis that provides liberated product in high purity, at a significantly enhanced rate. Herein we describe the implementation of a chiral auxiliary as a solid-phase linker, the detailed investigation of its unique aminolysis, and the utility of this cleavage within a chemical diversity format.

Org. Lett. (Organic letters)
[2002, 4(9):1419-1422]

Cited: 3 times

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