Catalytic Enantioselective Protoboration of Disubstituted Allenes. Access to Alkenylboron Compounds in High Enantiomeric Purity | Zendy

Hwanjong Jang | Zendy; Byunghyuck Jung | Zendy; Amir H. Hoveyda | Zendy

Open Access

Catalytic Enantioselective Protoboration of Disubstituted Allenes. Access to Alkenylboron Compounds in High Enantiomeric Purity

Author(s) -

Hwanjong Jang,

Byunghyuck Jung,

Amir H. Hoveyda

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol5022417

Subject(s) - chemistry , enantioselective synthesis , allylic rearrangement , stereoselectivity , yield (engineering) , catalysis , enantiomer , selectivity , organic chemistry , medicinal chemistry , materials science , metallurgy

Proto-boryl additions to 1,1-disubstituted allenes in the presence of 1.0-5.0 mol % of chiral NHC-Cu complexes, B2(pin)2, and t-BuOH proceed to afford alkenyl-B(pin) products in up to 98% yield, >98:2 site selectivity, and 98:2 er. The enantiomerically enriched alkenylboron products can be converted to otherwise difficult-to-access alkenyl bromides, methyl ketones or carboxylic acids. What's more, the corresponding boronic acids may be used in highly stereoselective NHC-Cu-catalyzed allylic substitution reactions.

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