Literature DB >> 19128191

Attempts to improve the overall stereoselectivity of the Ireland-Claisen rearrangement.

Chi-Li Chen1, Kosuke Namba, Yoshito Kishi.   

Abstract

With focus on the steric effects present in the transition states for the [3,3]-sigmatropic rearrangement, the substrate 5 has been designed to improve the overall stereoselectivity of the Ireland-Claisen rearrangement. Experimentally, it has been found that (1) only Z-6 rearranges to 7 at 80 degrees C and (2) E-6 isomerizes to Z-6 at 80 degrees C, thereby allowing the transformation of 5 into 7 in an almost quantitative yield. To illustrate the usefulness of this approach, two additional examples are given.

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Year:  2009        PMID： 19128191      PMCID： PMC2659616          DOI： 10.1021/ol8027225

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  9 in total

Review 1.  Claisen rearrangement over the past nine decades.

Authors:  Ana M Martín Castro
Journal:  Chem Rev       Date:  2004-06       Impact factor: 60.622

2.  A simple but remarkably effective device for forming the C8-C14 polycyclic ring system of halichondrin B.

Authors:  Kosuke Namba; Hyuk-Sang Jun; Yoshito Kishi
Journal:  J Am Chem Soc       Date:  2004-06-30       Impact factor: 15.419

3.  Halichondrin B: synthesis of the C1-C22 subunit.

Authors:  William T Lambert; Gregory H Hanson; Farid Benayoud; Steven D Burke
Journal:  J Org Chem       Date:  2005-11-11       Impact factor: 4.354

4.  Catalytic Ni/Cr-mediated macrocyclization without use of high-dilution techniques.

Authors:  Kosuke Namba; Yoshito Kishi
Journal:  J Am Chem Soc       Date:  2005-11-09       Impact factor: 15.419

5.  Highly functionalized pyranopyrans from furans: a synthesis of the C27-C38 and C44-C53 subunits of norhalichondrin B.

Authors:  James A Henderson; Katrina L Jackson; Andrew J Phillips
Journal:  Org Lett       Date:  2007-11-14       Impact factor: 6.005

6.  Further improvement on sulfonamide-based ligand for catalytic asymmetric 2-haloallylation and allylation.

Authors:  Zhiyu Zhang; Jian Huang; Bin Ma; Yoshito Kishi
Journal:  Org Lett       Date:  2008-06-13       Impact factor: 6.005

7.  Isolation and structure of the cell growth inhibitory constituents from the western Pacific marine sponge Axinella sp.

Authors:  G R Pettit; C L Herald; M R Boyd; J E Leet; C Dufresne; D L Doubek; J M Schmidt; R L Cerny; J N Hooper; K C Rützler
Journal:  J Med Chem       Date:  1991-11       Impact factor: 7.446

8.  Synthesis of the C29-C44 portion of spongistatin 1 (altohyrtin A).

Authors:  G A Wallace; R W Scott; C H Heathcock
Journal:  J Org Chem       Date:  2000-06-30       Impact factor: 4.354

9.  Operationally simple and efficient workup procedure for TBAF-mediated desilylation: application to halichondrin synthesis.

Authors:  Yosuke Kaburagi; Yoshito Kishi
Journal:  Org Lett       Date:  2007-02-15       Impact factor: 6.005
  9 in total
  5 in total

1.  Total synthesis of (-)-sessilifoliamide C and (-)-8-epi-stemoamide.

Authors:  Adam T Hoye; Peter Wipf
Journal:  Org Lett       Date:  2011-04-21       Impact factor: 6.005

2.  Combining a Clostridial enzyme exhibiting unusual active site plasticity with a remarkably facile sigmatropic rearrangement: rapid, stereocontrolled entry into densely functionalized fluorinated phosphonates for chemical biology.

Authors:  Kaushik Panigrahi; Gregory A Applegate; Guillaume Malik; David B Berkowitz
Journal:  J Am Chem Soc       Date:  2015-03-05       Impact factor: 15.419

3.  Computational study of factors controlling the boat and chair transition states of Ireland-Claisen rearrangements.

Authors:  Seref Gül; Franziska Schoenebeck; Viktorya Aviyente; K N Houk
Journal:  J Org Chem       Date:  2010-03-19       Impact factor: 4.354

4.  A Computational Study of the Origin of Stereoinduction in NHC-Catalyzed Annulation Reactions of α,β-Unsaturated Acyl Azoliums.

Authors:  Eirik Lyngvi; Jeffrey W Bode; Franziska Schoenebeck
Journal:  Chem Sci       Date:  2012-03-01       Impact factor: 9.825

5.  Second generation synthesis of C27-C35 building block of E7389, a synthetic halichondrin analogue.

Authors:  Yu-Rong Yang; Dae-Shik Kim; Yoshito Kishi
Journal:  Org Lett       Date:  2009-10-15       Impact factor: 6.005
  5 in total

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