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. 2011 Oct 5;133(39):15308-11.
doi: 10.1021/ja2064395. Epub 2011 Sep 14.

Catalytic asymmetric thiofunctionalization of unactivated alkenes

Scott E Denmark  1 , David J P Kornfilt, Thomas Vogler
Affiliations

Catalytic asymmetric thiofunctionalization of unactivated alkenes

Scott E Denmark et al. J Am Chem Soc. .

Abstract

Catalytic asymmetric sulfenylation of double bonds has been achieved using a BINAM-based phosphoramide catalyst and an electrophilic sulfur source. Simple alkenes as well as styrenes afforded sulfenylated tetrahydrofurans and tetrahydropyrans by closure with pendant hydroxyl or carboxyl groups. Intermolecular thiofunctionalizations were also achieved with simple alcohols or carboxylic acids as the nucleophiles.

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Figures

Figure 1
Figure 1
Proposed catalytic cycle for asymmetric sulfenofunctionalization.
Scheme 1
Scheme 1
Chart 1
Chart 1
See this image and copyright information in PMC

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