A multicomponent approach for the preparation of homoallylic alcohols.

Here we report the in situ generation of transient allylic boronic species, by reacting TMSCHN2 and E-vinyl boronic acids, followed by their subsequent trapping with aldehydes as electrophiles to yield homoallylic alcohols. This metal-free reaction was initially discovered by the use of a flow chemistry approach to generate a variety of homoallylic alcohols in a straightforward fashion and then transferred to a batch protocol.

Keywords

3405 Organic Chemistry, 34 Chemical Sciences

Journal Title

Chem Sci

Journal ISSN

2041-6520
2041-6539

Publisher

Royal Society of Chemistry (RSC)

Publisher DOI

https://doi.org/10.1039/c6sc02581a

Rights and licensing

Except where otherwised noted, this item's license is described as Attribution 4.0 International

Sponsorship

Engineering and Physical Sciences Research Council (EP/K009494/1)
Engineering and Physical Sciences Research Council (EP/K039520/1)

We are grateful to the Cambridge Home and European Scholarship Scheme (J. S. P.), Croucher Foundation (S. H. L.), the Swiss National Science Foundation (D. N. T.), Pfizer Worldwide Research & Development (C. B.), and the Engineering and Physical Sciences Research Council (S. V. L. grant no. EP/K0099494/1 and EP/K039520/1) for financial support.

Relationships

Is supplemented by:

https://doi.org/10.17863/CAM.591

Collections

Scholarly Works - Chemistry
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