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. 2010 Sep 3;12(17):3796-9.
doi: 10.1021/ol101472k.

Allylation of nitrosobenzene with pinacol allylboronates. A regioselective complement to peroxide oxidation

Robert E Kyne  1 , Michael C Ryan, Laura T Kliman, James P Morken
Affiliations

Allylation of nitrosobenzene with pinacol allylboronates. A regioselective complement to peroxide oxidation

Robert E Kyne et al. Org Lett. .

Abstract

Addition of nitrosobenzene to pinacol allylboronates leads to oxidation of the organoboron with concomitant rearrangement of the substrate alkene. This reaction appears to proceed by allylboration of the nitroso group in analogy to carbonyl and imine allylation reactions. Remarkably, the N-O bond is cleaved during the reaction such that simple alcohols are the final reaction product.

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Figures

Scheme 1
Scheme 1
Reaction of Nitrosobenzene with Allylboronate 2
Scheme 2
Scheme 2
Proposed Mechanism for N-O Bond Cleavage
Scheme 3
Scheme 3
Diastereoinduction in the Oxidation of Chiral Allylboronate 6
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