Literature DB >> 20355731

Highly diastereoselective preparation of homoallylic alcohols containing two contiguous quaternary stereocenters in acyclic systems from simple terminal alkynes.

Bishnu Dutta1, Noga Gilboa, Ilan Marek.   

Abstract

The combined carbocupration of terminal alkynes followed by a zinc homologation and further reaction with ketones lead, in a single-pot operation, to the creation of homoallylic alcohols possessing two consecutive quaternary stereocenters with excellent diastereoselectivity.

Entities:  

Year:  2010        PMID： 20355731     DOI： 10.1021/ja101371x

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


  11 in total

1.  Axial preferences in allylations via the Zimmerman-Traxler transition state.

Authors:  Noga Gilboa; Hao Wang; Kendall N Houk; Ilan Marek
Journal:  Chemistry       Date:  2011-06-03       Impact factor: 5.236

2.  Synthesis of Homoallylic Alcohols with Acyclic Quaternary Centers through CoIII -Catalyzed Three-Component C-H Bond Addition to Internally Substituted Dienes and Carbonyls.

Authors:  Sun Dongbang; Zican Shen; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-01       Impact factor: 15.336

3.  Forming all-carbon quaternary stereogenic centres in acyclic systems from alkynes.

Authors:  Yury Minko; Morgane Pasco; Lukas Lercher; Mark Botoshansky; Ilan Marek
Journal:  Nature       Date:  2012-10-25       Impact factor: 49.962

Review 4.  Axial preferences in allylation reactions via the Zimmerman-Traxler transition state.

Authors:  Tom Mejuch; Noga Gilboa; Eric Gayon; Hao Wang; K N Houk; Ilan Marek
Journal:  Acc Chem Res       Date:  2013-05-14       Impact factor: 22.384

5.  Stereodefined trisubstituted enolates as a unique entry to all-carbon quaternary stereogenic centers in acyclic systems.

Authors:  Yury Minko; Morgane Pasco; Lukas Lercher; Ilan Marek
Journal:  Nat Protoc       Date:  2013-03-21       Impact factor: 13.491

6.  A multicomponent approach for the preparation of homoallylic alcohols.

Authors:  Jian-Siang Poh; Shing-Hing Lau; Iain G Dykes; Duc N Tran; Claudio Battilocchio; Steven V Ley
Journal:  Chem Sci       Date:  2016-07-08       Impact factor: 9.825

7.  Remote functionalization of hydrocarbons with reversibility enhanced stereocontrol.

Authors:  Alexandre Vasseur; Lionel Perrin; Odile Eisenstein; Ilan Marek
Journal:  Chem Sci       Date:  2015-03-03       Impact factor: 9.825

8.  Recent advances in transition-metal-catalyzed intermolecular carbomagnesiation and carbozincation.

Authors:  Kei Murakami; Hideki Yorimitsu
Journal:  Beilstein J Org Chem       Date:  2013-02-11       Impact factor: 2.883

9.  Stereoselective synthesis of tetrasubstituted alkenes via a sequential carbocupration and a new sulfur-lithium exchange.

Authors:  Andreas Unsinn; Cora Dunst; Paul Knochel
Journal:  Beilstein J Org Chem       Date:  2012-12-18       Impact factor: 2.883

10.  Diastereodivergent combined carbometalation/zinc homologation/C-C fragmentation reaction as an efficient tool to prepare acyclic allylic quaternary carbon stereocenters.

Authors:  Sudipta Raha Roy; Dorian Didier; Amir Kleiner; Ilan Marek
Journal:  Chem Sci       Date:  2016-05-24       Impact factor: 9.825
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