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Modular evolution of a chiral auxiliary for the 1,3-dipolar cycloaddition of isomünchnones with vinyl ethers.

PMID: 11975592 (view PubMed database entry)
DOI: 10.1021/ol017263y (read at publisher's website )

Sergey N Savinov, David J Austin,

[reaction: see text]. The 1,3-dipolar cycloaddition reaction has long been recognized as a powerful methodology in organic synthesis. More recently, this reaction has become a popular manifold for the construction of chemical diversity. Herein, we report the development of a chiral template for the facially selective cycloaddition of isomünchnones, a common class of 1,3-dipoles. The modular format of the asymmetric unit allowed a systematic optimization of selectivity. In addition, the chiral auxiliary was removed through an unusually facile ester aminolysis.

Org. Lett. (Organic letters)
[2002, 4(9):1415-1418]

Cited: 1 time

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