Reductive Carbocyclization of Homoallylic Alcohols to  syn ‐Cyclobutanes by a Boron‐Catalyzed Dual Ring‐Closing Pathway | Zendy

Hazra Chinmoy Kumar | Zendy; Jeong Jinhoon | Zendy; Kim Hyunjoong | Zendy; Baik MuHyun | Zendy; Park Sehoon | Zendy; Chang Sukbok | Zendy

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Reductive Carbocyclization of Homoallylic Alcohols to syn ‐Cyclobutanes by a Boron‐Catalyzed Dual Ring‐Closing Pathway

Author(s) -

Hazra Chinmoy Kumar,

Jeong Jinhoon,

Kim Hyunjoong,

Baik MuHyun,

Park Sehoon,

Chang Sukbok

Publication year - 2018

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201713285

Subject(s) - cyclobutanes , chemistry , ring strain , catalysis , ring (chemistry) , scrambling , boron , reagent , reductive elimination , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , cycloaddition , linguistics , philosophy

The organoborane‐catalyzed reductive carbocyclization of homoallylic alcohols has been developed by using hydrosilanes as reducing reagents to provide a range of 1,2‐disubstituted arylcyclobutanes. The reaction proceeds in a cis ‐selective manner with high efficiency under mild conditions. Mechanistic studies, including deuterium scrambling and Hammett studies, and DFT calculations, suggest a dual ring‐closing pathway.

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