Literature DB >> 15496077

Asymmetric catalytic synthesis of enantiopure N-protected 1,2-amino alcohols.

Giuseppe Bartoli1, Marcella Bosco, Armando Carlone, Manuela Locatelli, Paolo Melchiorre, Letizia Sambri.   

Abstract

[reaction: see text] The asymmetric aminolytic kinetic resolution (AKR) of racemic terminal epoxides using carbamates as the nucleophile catalyzed by (salen)Co(III) complex provides a practical and straightforward method for the synthesis of both aliphatic and aromatic N-Boc- or N-Cbz-protected 1,2-amino alcohols in almost enantiomerically pure form (ee >/= 99%). The AKR uses an easily accessible catalyst and inexpensive starting materials, and the reactions are conveniently carried out at room temperature under an air atmosphere.

Entities:  

Year:  2004        PMID: 15496077     DOI: 10.1021/ol048322l

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  8 in total

1.  Multicomponent synthesis of dihydrobenzoxazepinones, bearing four diversity points, as potential α-helix mimics.

Authors:  Luca Banfi; Andrea Basso; Valentina Cerulli; Giuseppe Guanti; Paulina Lecinska; Ilaria Monfardini; Renata Riva
Journal:  Mol Divers       Date:  2009-11-28       Impact factor: 2.943

2.  Mechanistic basis for high reactivity of (salen)Co-OTs in the hydrolytic kinetic resolution of terminal epoxides.

Authors:  Lars P C Nielsen; Stephan J Zuend; David D Ford; Eric N Jacobsen
Journal:  J Org Chem       Date:  2012-02-08       Impact factor: 4.354

3.  A broadly applicable and practical oligomeric (salen) Co catalyst for enantioselective epoxide ring-opening reactions.

Authors:  David E White; Pamela M Tadross; Zhe Lu; Eric N Jacobsen
Journal:  Tetrahedron       Date:  2014-07-08       Impact factor: 2.457

4.  A practical method for the synthesis of highly enantioenriched trans-1,2-amino alcohols.

Authors:  James A Birrell; Eric N Jacobsen
Journal:  Org Lett       Date:  2013-06-06       Impact factor: 6.005

5.  Mechanistic basis for high stereoselectivity and broad substrate scope in the (salen)Co(III)-catalyzed hydrolytic kinetic resolution.

Authors:  David D Ford; Lars P C Nielsen; Stephan J Zuend; Charles B Musgrave; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2013-10-07       Impact factor: 15.419

6.  Enantioselective intramolecular openings of oxetanes catalyzed by (salen)Co(III) complexes: access to enantioenriched tetrahydrofurans.

Authors:  Rebecca N Loy; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2009-03-04       Impact factor: 15.419

7.  α,β-Aziridinylphosphonates by lithium amide-induced phosphonyl migration from nitrogen to carbon in terminal aziridines.

Authors:  David M Hodgson; Zhaoqing Xu
Journal:  Beilstein J Org Chem       Date:  2010-10-13       Impact factor: 2.883

8.  N-tert-Butoxycarbonylation of Structurally Diverse Amines and Sulfamides under Water-Mediated Catalyst-Free Conditions.

Authors:  Zinelaabine Cheraiet; Souad Ouarna; Sihem Hessainia; Malika Berredjem; Nour-Eddine Aouf
Journal:  ISRN Org Chem       Date:  2012-05-09
  8 in total

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