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Imine additions of internal alkynes for the synthesis of trisubstituted (E)-alkene and cyclopropane peptide isosteres

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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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Wipf, Ppwipf@pitt.eduPWIPF
Xiao, J
Geib, SJgeib@pitt.eduGEIB0000-0002-9160-7857
Date: 1 October 2005
Date Type: Publication
Journal or Publication Title: Advanced Synthesis and Catalysis
Volume: 347
Number: 11-13
Page Range: 1605 - 1613
DOI or Unique Handle: 10.1002/adsc.200505171
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1615-4150
Date Deposited: 18 Jul 2014 21:05
Last Modified: 02 Feb 2019 15:57
URI: http://d-scholarship.pitt.edu/id/eprint/22245

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