Wipf, P and Xiao, J and Geib, SJ
(2005)
Imine additions of internal alkynes for the synthesis of trisubstituted (E)-alkene and cyclopropane peptide isosteres.
Advanced Synthesis and Catalysis, 347 (11-13).
1605 - 1613.
ISSN 1615-4150
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Abstract
Divergent multi-component reactions (DMCR) involving C-C 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. C-C bond formation by microwave-accelerated Stille coupling of stannylalkenes represents a fast, convergent synthetic approach toward trisubstituted (E)-alkene dipeptide isosteres. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
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