Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 1, Pages 320-324Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201910397
Keywords
cross-coupling; lithium; natural products; palladium; zinc
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Funding
- FCI foundation
- [SFB749]
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We report palladium-catalyzed cross-coupling reactions of chiral secondary non-stabilized dialkylzinc reagents, prepared from readily available chiral secondary alkyl iodides, with alkenyl and aryl halides. This method provides alpha-chiral alkenes and arenes with very high retention of configuration (dr up to 98:2) and satisfactory overall yields (up to 76 % for 3 reaction steps). The configurational stability of these chiral non-stabilized dialkylzinc reagents was determined and exceeded several hours at 25 degrees C. DFT calculations were performed to rationalize the stereoretention during the catalytic cycle. Furthermore, the cross-coupling reaction was applied in an efficient total synthesis of the sesquiterpenes (S)- and (R)-curcumene with control of the absolute stereochemistry.
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