Literature DB >> 14505373

Four-component reactions for a new diastereoselective synthesis of chiral quaternary centers.

Genia Sklute1, Deborah Amsallem, Amal Shabli, Jos P Varghese, Ilan Marek.   

Abstract

The one-pot preparation of chiral homoallylic alcohol and amine derivatives was easily achieved by carbocupration of alkynyl sulfoxides followed by an in situ zinc homologation and reaction with aldehydes or imines. In this process, three new carbon-carbon bonds were created as well as quaternary and tertiary chiral centers with excellent diastereo- and enantioselectivities.

Entities:  

Year:  2003        PMID: 14505373     DOI: 10.1021/ja036872t

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


  7 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.  Recent advances in carbocupration of α-heterosubstituted alkynes.

Authors:  Ahmad Basheer; Ilan Marek
Journal:  Beilstein J Org Chem       Date:  2010-07-15       Impact factor: 2.883

Review 3.  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

4.  Diastereoselective ring opening of fully-substituted cyclopropanes via intramolecular Friedel-Crafts alkylation.

Authors:  Veeranjaneyulu Lanke; Fa-Guang Zhang; Alexander Kaushansky; Ilan Marek
Journal:  Chem Sci       Date:  2019-08-27       Impact factor: 9.825

5.  Synthesis and biological evaluation of the new ring system benzo[f]pyrimido[1,2-d][1,2,3]triazolo[1,5-a][1,4]diazepine and its cycloalkane and cycloalkene condensed analogues.

Authors:  Mohamed El Haimer; Márta Palkó; Matti Haukka; Márió Gajdács; István Zupkó; Ferenc Fülöp
Journal:  RSC Adv       Date:  2021-02-10       Impact factor: 3.361

6.  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

7.  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

  7 in total

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