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Imine Additions of Internal Alkynes for the Synthesis of Trisubstituted (E)‐Alkene and Cyclopropane Peptide Isosteres
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AbstractDivergent multi‐component reactions (DMCR) involving CC bond formations can provide large increases in structural diversity and allow the rapid assembly of complex products from readily available starting materials. Cascade hydrozirconation‐Zr/Zn transmetalation‐imine addition of alkynes represents a versatile methodology for the synthesis of (E)‐alkene and cyclopropane dipeptide isosteres. Appropriate substitutions at the sp2‐carbon of (E)‐alkene peptide isosteres allow a range of Pd‐catalyzed cross‐coupling reactions, which can be used for the fine‐tuning of the conformational and electronic properties of the parent peptide bond mimic. CC bond formation by microwave‐accelerated Stille coupling of stannylalkenes represents a fast, convergent synthetic approach toward trisubstituted (E)‐alkene dipeptide isosteres.
Title: Imine Additions of Internal Alkynes for the Synthesis of Trisubstituted (E)‐Alkene and Cyclopropane Peptide Isosteres
Description:
AbstractDivergent multi‐component reactions (DMCR) involving CC bond formations can provide large increases in structural diversity and allow the rapid assembly of complex products from readily available starting materials.
Cascade hydrozirconation‐Zr/Zn transmetalation‐imine addition of alkynes represents a versatile methodology for the synthesis of (E)‐alkene and cyclopropane dipeptide isosteres.
Appropriate substitutions at the sp2‐carbon of (E)‐alkene peptide isosteres allow a range of Pd‐catalyzed cross‐coupling reactions, which can be used for the fine‐tuning of the conformational and electronic properties of the parent peptide bond mimic.
CC bond formation by microwave‐accelerated Stille coupling of stannylalkenes represents a fast, convergent synthetic approach toward trisubstituted (E)‐alkene dipeptide isosteres.
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