Literature DB >> 21247165

A new family of cinchona-derived amino phosphine precatalysts: application to the highly enantio- and diastereoselective silver-catalyzed isocyanoacetate aldol reaction.

Filippo Sladojevich1, Andrea Trabocchi, Antonio Guarna, Darren J Dixon.   

Abstract

A new class of readily accessible chiral amino-phosphine precatalysts derived from 9-amino(9-deoxy) epicinchona alkaloids has been developed. In combination with Ag(I) salts, these amino-phosphines performed as effective cooperative Brønsted base/Lewis acid catalysts in the asymmetric aldol reaction of isocyanoacetate nucleophiles. Under optimal conditions, high diastereoselectivities (up to 98%) and enantioselectivities (up to 98%) were obtained.

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Year:  2011        PMID： 21247165     DOI： 10.1021/ja110534g

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


  14 in total

1.  Generation of stereochemically defined tetrasubstituted enolborinates by 1,4-hydroboration of α,β-unsaturated morpholine carboxamides with (diisopinocampheyl)borane.

Authors:  Christophe Allais; Andy S Tsai; Philippe Nuhant; William R Roush
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-15       Impact factor: 15.336

2.  A general asymmetric copper-catalysed Sonogashira C(sp3)-C(sp) coupling.

Authors:  Xiao-Yang Dong; Yu-Feng Zhang; Can-Liang Ma; Qiang-Shuai Gu; Fu-Li Wang; Zhong-Liang Li; Sheng-Peng Jiang; Xin-Yuan Liu
Journal:  Nat Chem       Date:  2019-10-21       Impact factor: 24.427

3.  Catalytic Isonitrile Insertions and Condensations Initiated by RNC-X Complexation.

Authors:  Suravi Chakrabarty; Shruti Choudhary; Arpit Doshi; Fa-Qiang Liu; Rishabh Mohan; Manasa P Ravindra; Dhruv Shah; Xun Yang; Fraser F Fleming
Journal:  Adv Synth Catal       Date:  2014-06-20       Impact factor: 5.837

4.  Synthesis and evaluation of cyclopentane-based muraymycin analogs targeting MraY.

Authors:  Seung-Hwa Kwak; Won Young Lim; Aili Hao; Ellene H Mashalidis; Do-Yeon Kwon; Pyeonghwa Jeong; Mi Jung Kim; Seok-Yong Lee; Jiyong Hong
Journal:  Eur J Med Chem       Date:  2021-02-06       Impact factor: 6.514

5.  Catalytic Asymmetric Direct Aldol Reaction of α-Alkyl Azlactones and Aliphatic Aldehydes.

Authors:  Yang Zheng; Li Deng
Journal:  Chem Sci       Date:  2015-08-04       Impact factor: 9.825

6.  Direct catalytic enantio- and diastereoselective ketone aldol reactions of isocyanoacetates.

Authors:  Raquel de la Campa; Irene Ortín; Darren J Dixon
Journal:  Angew Chem Int Ed Engl       Date:  2015-03-03       Impact factor: 15.336

7.  Enantioselective synthesis of (-)-chloramphenicol via silver-catalysed asymmetric isocyanoacetate aldol reaction.

Authors:  Allegra Franchino; Pavol Jakubec; Darren J Dixon
Journal:  Org Biomol Chem       Date:  2016-01-07       Impact factor: 3.876

8.  A catalytic highly enantioselective allene approach to oxazolines.

Authors:  Hongwen Luo; Zheng Yang; Weilong Lin; Yangguangyan Zheng; Shengming Ma
Journal:  Chem Sci       Date:  2018-01-05       Impact factor: 9.825

9.  Addition of H-phosphonates to quinine-derived carbonyl compounds. An unexpected C9 phosphonate-phosphate rearrangement and tandem intramolecular piperidine elimination.

Authors:  Lukasz Górecki; Artur Mucha; Paweł Kafarski
Journal:  Beilstein J Org Chem       Date:  2014-04-17       Impact factor: 2.883

10.  Asymmetric Synthesis of Spiropyrazolones by Sequential Organo- and Silver Catalysis.

Authors:  Daniel Hack; Alexander B Dürr; Kristina Deckers; Pankaj Chauhan; Nico Seling; Lukas Rübenach; Lucas Mertens; Gerhard Raabe; Franziska Schoenebeck; Dieter Enders
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-16       Impact factor: 15.336
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