期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 1, 页码 320-324出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201910397
关键词
cross-coupling; lithium; natural products; palladium; zinc
资金
- FCI foundation
- [SFB749]
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.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据