Literature DB >> 18561353

A shift in retrosynthetic paradigm.

Ilan Marek1.   

Abstract

The current state-of-the-art synthesis for the formation of enantiomerically enriched all-carbon quaternary stereocenters in acyclic system relies on the formation of a single carbon-carbon bond per chemical step by asymmetric catalysis. These extraordinary sophisticated methods were logically classified among the most powerful and innovative ones. In this concept article, we are proposing a new retrosynthetic paradigm to solve differently such challenging problems. These new synthetic pathways lead to the diastereo- and enantiomerically pure formation of three new carbon-carbon bonds in acyclic system, in a one-pot reaction, including the formation of all-carbon quaternary stereocenters by using classical reagents and experimental conditions and from common starting materials.

Entities:  

Year:  2008        PMID: 18561353     DOI: 10.1002/chem.200800580

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  8 in total

1.  A unique approach to aldol products for the creation of all-carbon quaternary stereocentres.

Authors:  Jaya Prakash Das; Helena Chechik; Ilan Marek
Journal:  Nat Chem       Date:  2009-03-29       Impact factor: 24.427

2.  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

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

4.  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

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.  Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres.

Authors:  Zackaria Nairoukh; Gunda G K S Narayana Kumar; Yury Minko; Ilan Marek
Journal:  Chem Sci       Date:  2016-09-15       Impact factor: 9.825

7.  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

8.  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

  8 in total

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