TY - JOUR
T1 - Cobalt-Catalyzed Intramolecular Reactions between a Vinylcyclopropane and an Alkyne
T2 - Switchable [5+2] Cycloaddition and Homo-Ene Pathways
AU - Wu, Chunlin
AU - Yoshikai, Naohiko
N1 - Funding Information:
This research was funded by the Ministry of Education (Singapore) and Nanyang Technological University (RG 3/15, RG 114/15, and MOE2016-T2-2-043). The High-Performance Computing Centre of NTU is acknowledged for computer resources. We thank Dr. Yongxin Li and Dr. Rakesh Ganguly (Nanyang Technological University) for assistance with X-ray crystallographic analysis.
Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2018/5/28
Y1 - 2018/5/28
N2 - Cobalt–diphosphine catalysts have been found to promote intramolecular reactions between a vinylcyclopropane and an alkyne to selectively afford either the [5+2] cycloaddition product or the homo-ene reaction product under solvent control. The former product is exclusively formed in noncoordinating 1,2-dichloroethane, whereas the latter is dominant in coordinating solvents, such as acetonitrile and dimethylacetamide. Furthermore, a highly enantioselective variant of the homo-ene reaction afforded chiral tetrahydrofuran, pyrrolidine, and cyclopentane derivatives bearing 1,3-diene and alkylidene substituents.
AB - Cobalt–diphosphine catalysts have been found to promote intramolecular reactions between a vinylcyclopropane and an alkyne to selectively afford either the [5+2] cycloaddition product or the homo-ene reaction product under solvent control. The former product is exclusively formed in noncoordinating 1,2-dichloroethane, whereas the latter is dominant in coordinating solvents, such as acetonitrile and dimethylacetamide. Furthermore, a highly enantioselective variant of the homo-ene reaction afforded chiral tetrahydrofuran, pyrrolidine, and cyclopentane derivatives bearing 1,3-diene and alkylidene substituents.
KW - asymmetric catalysis
KW - cobalt
KW - cycloaddition
KW - cyclopropanes
KW - C−C bond cleavage
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U2 - 10.1002/anie.201803162
DO - 10.1002/anie.201803162
M3 - Article
C2 - 29659114
AN - SCOPUS:85046477154
VL - 57
SP - 6558
EP - 6562
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 22
ER -