4.4 Article

Citric acid mediated catalytic osmylation/oxidative cleavage of electron deficient olefins: a vinyl sulfone study

Journal

TETRAHEDRON LETTERS
Volume 56, Issue 28, Pages 4151-4154

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.05.044

Keywords

Acyloin; Osmium catalysis; Electron deficient olefins; Vinyl sulfone; Polyketide; Oxidative cleavage

Funding

  1. Purdue University

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The first broad catalytic dihydroxylation of enantiopure cyclic vinyl sulfones followed by oxidative cleavage of the resulting acyloin provides linear termini-differentiated polyketide fragments. This mild vinyl sulfone cleavage provides an effective alternative to the current ozonolysis protocol. (C) 2015 Elsevier Ltd. All rights reserved.

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