Literature DB >> 14570453

Catalyzed olefin isomerization leading to highly stereoselective Claisen rearrangements of aliphatic allyl vinyl ethers.

Scott G Nelson1, Christopher J Bungard, Kan Wang.   

Abstract

Iridium(I)-catalyzed olefin isomerization in bis(allyl) ethers is integrated into a generally applicable strategy for affecting highly stereoselective Claisen rearrangements. Catalyzed alkene isomerization affords allyl vinyl ethers from easily prepared di(allyl) ethers; direct thermolysis of these reaction mixtures leads to highly diastereoselective [3,3] sigmatropic rearrangements affording syn-2,3-dialkyl-4-pentenal derivatives. An easily executed strategy for realizing asymmetric variants of the isomerization-Claisen rearrangement (ICR) reactions is also described.

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Year:  2003        PMID： 14570453     DOI： 10.1021/ja037655v

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  15 in total

1.  Direct, iridium-catalyzed enantioselective and regioselective allylic etherification with aliphatic alcohols.

Authors:  Satoshi Ueno; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  Iridium-catalyzed allylation of chiral β-stereogenic alcohols: bypassing discrete formation of epimerizable aldehydes.

Authors:  Daniel C Schmitt; Anne-Marie R Dechert-Schmitt; Michael J Krische
Journal:  Org Lett       Date:  2012-12-11       Impact factor: 6.005

Review 3.  Toward a symphony of reactivity: cascades involving catalysis and sigmatropic rearrangements.

Authors:  Amanda C Jones; Jeremy A May; Richmond Sarpong; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-03       Impact factor: 15.336

4.  Chiral N-Heterocyclic Carbene Catalyzed Annulations of Enals and Ynals with Stable Enols: A Highly Enantioselective Coates-Claisen Rearrangement.

Authors:  Jessada Mahatthananchai; Juthanat Kaeobamrung; Jeffrey W Bode
Journal:  ACS Catal       Date:  2012-02-29       Impact factor: 13.084

5.  De novo asymmetric synthesis of milbemycin beta3 via an iterative asymmetric hydration approach.

Authors:  Miaosheng Li; George A O'Doherty
Journal:  Org Lett       Date:  2006-08-31       Impact factor: 6.005

6.  A tandem isomerization/prins strategy: iridium(III)/Brønsted acid cooperative catalysis.

Authors:  Vince M Lombardo; Christopher D Thomas; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-11       Impact factor: 15.336

7.  Syntheses and structural confirmations of members of a heterocycle-containing family of labdane diterpenoids.

Authors:  Daniel J Mack; Jon T Njardarson
Journal:  Angew Chem Int Ed Engl       Date:  2012-12-17       Impact factor: 15.336

8.  Facile Pd(II)- and Ni(II)-catalyzed isomerization of terminal alkenes into 2-alkenes.

Authors:  Hwan Jung Lim; Craig R Smith; T V RajanBabu
Journal:  J Org Chem       Date:  2009-06-19       Impact factor: 4.354

9.  [4 + 2] cycloadditions of N-alkenyl iminium ions: structurally complex heterocycles from a three-component Diels-Alder reaction sequence.

Authors:  Nihar Sarkar; Abhisek Banerjee; Scott G Nelson
Journal:  J Am Chem Soc       Date:  2008-06-25       Impact factor: 15.419

10.  Ru-catalyzed isomerization of ω-alkenylboronates towards stereoselective synthesis of vinylboronates with subsequent in situ functionalization.

Authors:  Guo-Ming Ho; Lucas Segura; Ilan Marek
Journal:  Chem Sci       Date:  2020-05-26       Impact factor: 9.825
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