Literature DB >> 23742206

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

James A Birrell1, Eric N Jacobsen.   

Abstract

A highly enantioselective addition of phenyl carbamate to meso-epoxides has been developed to efficiently generate protected trans-1,2-amino alcohols. This transformation is promoted by an oligomeric (salen)Co-OTf catalyst and has been used to prepare two useful 2-aminocycloalkanol hydrochlorides in enantiopure form on a multigram scale from commercially available starting materials.

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Year:  2013        PMID： 23742206      PMCID： PMC3815482          DOI： 10.1021/ol401013s

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


  22 in total

1.  Highly active oligomeric (salen)co catalysts for asymmetric epoxide ring-opening reactions.

Authors:  J M Ready; E N Jacobsen
Journal:  J Am Chem Soc       Date:  2001-03-21       Impact factor: 15.419

2.  Enantioselective epoxide polymerization using a bimetallic cobalt catalyst.

Authors:  Renee M Thomas; Peter C B Widger; Syud M Ahmed; Ryan C Jeske; Wataru Hirahata; Emil B Lobkovsky; Geoffrey W Coates
Journal:  J Am Chem Soc       Date:  2010-11-02       Impact factor: 15.419

3.  A practical oligomeric [(salen)Co] catalyst for asymmetric epoxide ring-opening reactions.

Authors:  Joseph M Ready; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2002-04-15       Impact factor: 15.336

4.  Degradation and reconstruction of moenomycin A and derivatives: dissecting the function of the isoprenoid chain.

Authors:  Masaatsu Adachi; Yi Zhang; Catherine Leimkuhler; Binyuan Sun; John V LaTour; Daniel E Kahne
Journal:  J Am Chem Soc       Date:  2006-11-01       Impact factor: 15.419

5.  Enantioselective ring opening of meso-epoxides by aromatic amines catalyzed by lanthanide iodo binaphtholates.

Authors:  Fabien Carrée; Richard Gil; Jacqueline Collin
Journal:  Org Lett       Date:  2005-03-17       Impact factor: 6.005

6.  An enantioselective total synthesis of (+)-peloruside A.

Authors:  Meredeth A McGowan; Christian P Stevenson; Matthew A Schiffler; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2010-08-16       Impact factor: 15.336

7.  Ring-expanding olefin metathesis: a route to highly active unsymmetrical macrocyclic oligomeric co-salen catalysts for the hydrolytic kinetic resolution of epoxides.

Authors:  Xiaolai Zheng; Christopher W Jones; Marcus Weck
Journal:  J Am Chem Soc       Date:  2007-02-07       Impact factor: 15.419

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

Authors:  Giuseppe Bartoli; Marcella Bosco; Armando Carlone; Manuela Locatelli; Paolo Melchiorre; Letizia Sambri
Journal:  Org Lett       Date:  2004-10-28       Impact factor: 6.005

9.  Palladium-catalyzed regioselective hydrodebromination of dibromoindoles: application to the enantioselective synthesis of indolodioxane U86192A.

Authors:  Junghyun Chae; Stephen L Buchwald
Journal:  J Org Chem       Date:  2004-05-14       Impact factor: 4.354

10.  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
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  6 in total

1.  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

2.  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

3.  γ-, Diastereo-, and Enantioselective Addition of MEMO-Substituted Allylboron Compounds to Aldimines Catalyzed by Organoboron-Ammonium Complexes.

Authors:  Ryan J Morrison; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-01       Impact factor: 15.336

4.  Catalytic Annulation of Epoxides with Heterocumulenes by the Indium-Tin System.

Authors:  Itaru Suzuki; Akira Imakuni; Akio Baba; Ikuya Shibata
Journal:  Molecules       Date:  2018-03-28       Impact factor: 4.411

5.  General approach to the synthesis of the chlorosulfolipids danicalipin A, mytilipin A, and malhamensilipin A in enantioenriched form.

Authors:  Won-jin Chung; Joseph S Carlson; Christopher D Vanderwal
Journal:  J Org Chem       Date:  2014-02-13       Impact factor: 4.354

6.  Enzymatic synthesis of chiral amino-alcohols by coupling transketolase and transaminase-catalyzed reactions in a cascading continuous-flow microreactor system.

Authors:  Pia Gruber; Filipe Carvalho; Marco P C Marques; Brian O'Sullivan; Fabiana Subrizi; Dragana Dobrijevic; John Ward; Helen C Hailes; Pedro Fernandes; Roland Wohlgemuth; Frank Baganz; Nicolas Szita
Journal:  Biotechnol Bioeng       Date:  2017-11-09       Impact factor: 4.530
  6 in total

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