Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 52, Pages 11971-11973Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202002297
Keywords
copper; cross-coupling; lithium; stereoselectivity
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Funding
- DFG
- FCI-foundation
- Projekt DEAL
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Chiral secondary alkylcopper reagents were prepared from the corresponding alkyl iodides with retention of configuration by an I/Li-exchange usingtBuLi (-100 degrees C, 1 min) followed by a transmetalation with CuBr.P(OEt)(3)(-100 degrees C, 20 s). These stereodefined secondary alkylcoppers underwent stereoretentive cross-couplings with several 3-iodo or 3-bromo unsaturated carbonyl derivatives leading to the corresponding gamma-methylated Michael acceptors in good yields and with high diastereoselectivities (dr up to 96:4). The method was extended to enantiomerically enriched alkylcoppers, providing optically enriched advanced natural product intermediates with up to 90 %ee.
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