Premium
Imine Additions of Internal Alkynes for the Synthesis of Trisubstituted ( E )‐Alkene and Cyclopropane Peptide Isosteres
Author(s) -
Wipf Peter,
Xiao Jingbo,
Geib Steven J.
Publication year - 2005
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200505171
Subject(s) - chemistry , alkene , cyclopropane , dipeptide , imine , transmetalation , stille reaction , stereochemistry , peptide bond , alkyne , bond cleavage , combinatorial chemistry , peptide , organic chemistry , ring (chemistry) , catalysis , biochemistry
Divergent 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 sp 2 ‐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.