4.7 Article

Identifying a non-chiral ligand for the efficient chirality transfer in carbonylation of propargylic mesylates

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 1, Issue 7, Pages 807-811

Publisher

CHINESE CHEMICAL SOC
DOI: 10.1039/c4qo00151f

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Enantioselective synthesis of optically active 2,4-disubstituted 2,3-allenoates has been realized with a very high chirality transfer efficiency using the inexpensive commercially available non-chiral DPEphos in the presence of 100-200 psi of CO at room temperature. The key for the high efficiency of this chirality transfer process has been certified as the matched coordination of Pd with DPEphos forming a relatively stable optically active square planar allenylic Pd(II) complex, which undergoes a facile carbonylation in the presence of 10 equiv. of BnOH and 100-200 psi of CO.

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