期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 26, 期 52, 页码 11971-11973出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202002297
关键词
copper; cross-coupling; lithium; stereoselectivity
资金
- DFG
- FCI-foundation
- Projekt DEAL
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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