Olefin Functionalization/Isomerization Enables Stereoselective Alkene Synthesis.
Nat Catal
; 4(8): 674-683, 2021 Aug.
Article
em En
| MEDLINE
| ID: mdl-36051572
ABSTRACT
Despite tremendous efforts aimed at devising methods for stereoselective alkene synthesis, critical challenges are yet to be addressed. Direct access to a diverse range of 1aryl(boryl)-1-methyl-functionalized tri- and tetrasubstituted trans alkenes, entities that are prevalent in many important molecules of interest, through a catalytic manifold from readily available α-olefin substrates remains elusive. Here, we demonstrate that catalytic amounts of a nonprecious N-heterocyclic carbene-Ni(I) complex in conjunction with a sterically bulky base promote site- and trans-selective union of monosubstituted olefins with a wide array of electrophilic reagents to deliver tri- and tetrasubstituted alkenes in up to 92% yield and >98% regio- and stereoselectivity. The protocol is amenable to the preparation of carbon- and heteroatom-substituted C=C bonds, providing distinct advantages over existing transformations. Utility is highlighted through concise stereoselective synthesis of biologically active compounds.
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MEDLINE
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En
Ano de publicação:
2021
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Article