Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 3, Pages 821-826Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201611444
Keywords
boron; copper; enantioselective catalysis; enantioselective synthesis; multicomponent reactions
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Funding
- NIH [GM-47480]
- National Science Foundation [CHE-1362763]
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A highly chemo-, diastereo- and enantioselective catalytic method that efficiently combines a silyl hydride, vinyl-B(pin) (pin-pinacolato) and (E)-1,2-disubstituted allylic phosphates is introduced. Reactions, best promoted by a Cu-based complex with a chiral sulfonate-containing N-heterocyclic carbene, are broadly applicable. Aryl-, heteroaryl-, alkenyl-, alkynyl- and alkyl-substituted allylic phosphates may thus be converted to the corresponding homoallylic boronates and then alcohols (after C-B bond oxidation) in 46-91% yield and in up to >98% S(N)2':S(N)2 ratio, 96:4 diastereomeric ratio and 98:2 enantiomeric ratio. The reasons why an NHC-Cu catalyst is uniquely effective (vs. the corresponding phosphine systems) and the basis for different trends in stereoselectivity are provided with the aid of DFT calculations.
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