Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 2, Pages 613-617Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201409104
Keywords
alkenes; aminoboration; copper; synthetic methods; umpolung
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Funding
- MEXT
- JSPS (Japan)
- Grants-in-Aid for Scientific Research [25620084] Funding Source: KAKEN
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A copper-catalyzed aminoboration of bicyclic alkenes, including oxa- and azabenzonorbornadienes, has been developed. With this method, amine and boron moieties are simultaneously introduced at an olefin with exo selectivity. Subsequent stereospecific transformations of the boryl group can provide oxygen- and nitrogen-rich cyclic molecules with motifs that may be found in natural products or pharmaceutically active compounds. Moreover, a catalytic asymmetric variant of this transformation was realized by using a copper complex with a chiral bisphosphine ligand, namely (R,R)-Ph-BPE.
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