TY - JOUR
T1 - Modular Cyclopentenone Synthesis through the Catalytic Molecular Shuffling of Unsaturated Acid Chlorides and Alkynes
AU - Lee, Yong Ho
AU - Denton, Elliott H.
AU - Morandi, Bill
N1 - Funding Information:
The financial support by the European Research Council under the European Union’s Horizon 2020 research and innovation program (Shuttle Cat, Project ID: 757608), the ETH Zürich, and LG Chem (fellowship to Y.H.L.) is gratefully acknowledged. We thank the NMR, MS (MoBiAS), and X-ray (SMoCC) service departments at ETH Zürich for technical assistance. We are also grateful to Prof. E. M. Carreira for sharing chiral GC and M. Isomura and V. Gerken for technical help.
Publisher Copyright:
© 2020 American Chemical Society.
PY - 2020/12/16
Y1 - 2020/12/16
N2 - We describe a general strategy for the intermolecular synthesis of polysubstituted cyclopentenones using palladium catalysis. Overall, this reaction is achieved via a molecular shuffling process involving an alkyne, an α,β-unsaturated acid chloride, which serves as both the alkene and carbon monoxide source, and a hydrosilane to create three new C-C bonds. This new carbon monoxide-free pathway delivers the products with excellent yields. Furthermore, the regioselectivity is complementary to conventional methods for cyclopentenone synthesis. In addition, a set of regio- and chemodivergent reactions are presented to emphasize the synthetic potential of this novel strategy.
AB - We describe a general strategy for the intermolecular synthesis of polysubstituted cyclopentenones using palladium catalysis. Overall, this reaction is achieved via a molecular shuffling process involving an alkyne, an α,β-unsaturated acid chloride, which serves as both the alkene and carbon monoxide source, and a hydrosilane to create three new C-C bonds. This new carbon monoxide-free pathway delivers the products with excellent yields. Furthermore, the regioselectivity is complementary to conventional methods for cyclopentenone synthesis. In addition, a set of regio- and chemodivergent reactions are presented to emphasize the synthetic potential of this novel strategy.
UR - http://www.scopus.com/inward/record.url?scp=85097802719&partnerID=8YFLogxK
U2 - 10.1021/jacs.0c10832
DO - 10.1021/jacs.0c10832
M3 - Article
C2 - 33284017
AN - SCOPUS:85097802719
SN - 0002-7863
VL - 142
SP - 20948
EP - 20955
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 50
ER -