Literature DB >> 22535485

Diastereoselective synthesis of vicinal amino alcohols.

Oskari K Karjalainen1, Ari M P Koskinen.   

Abstract

The vicinal amino alcohol is a common motif in natural products and pharmaceuticals. Amino acids constitute a natural, inexpensive, and enantiopure choice of starting material for the synthesis of such functionalities. However, the matters concerning diastereoselectivity are not obvious. This Perspective takes a look in the field of diastereoselective synthesis of vicinal amino alcohols starting from amino acids using various methods.

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Year:  2012        PMID: 22535485     DOI: 10.1039/c2ob25357g

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  15 in total

1.  2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones.

Authors:  Kangnan Li; Xinxin Shao; Luke Tseng; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2018-01-04       Impact factor: 15.419

2.  Directed β C-H Amination of Alcohols via Radical Relay Chaperones.

Authors:  Ethan A Wappes; Kohki M Nakafuku; David A Nagib
Journal:  J Am Chem Soc       Date:  2017-07-25       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.  A Diastereodivergent and Enantioselective Approach to syn- and anti-Diamines: Development of 2-Azatrienes for Cu-Catalyzed Reductive Couplings with Imines That Furnish Allylic Amines.

Authors:  Pengfei Zhou; Xinxin Shao; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2021-08-23       Impact factor: 16.383

5.  Concise, stereodivergent and highly stereoselective synthesis of cis- and trans-2-substituted 3-hydroxypiperidines - development of a phosphite-driven cyclodehydration.

Authors:  Peter H Huy; Julia C Westphal; Ari M P Koskinen
Journal:  Beilstein J Org Chem       Date:  2014-02-11       Impact factor: 2.883

Review 6.  Garner's aldehyde as a versatile intermediate in the synthesis of enantiopure natural products.

Authors:  Mikko Passiniemi; Ari Mp Koskinen
Journal:  Beilstein J Org Chem       Date:  2013-11-26       Impact factor: 2.883

7.  The Industrial Age of Biocatalytic Transamination.

Authors:  Michael Fuchs; Judith E Farnberger; Wolfgang Kroutil
Journal:  European J Org Chem       Date:  2015-09-23

8.  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

9.  Access to a Catalytically Generated Umpolung Reagent through the Use of Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral Vicinal Aminoalcohol Synthons.

Authors:  Samantha L Gargaro; Raphael K Klake; Kevin L Burns; Sharon O Elele; Skyler L Gentry; Joshua D Sieber
Journal:  Org Lett       Date:  2019-11-26       Impact factor: 6.005

10.  In situ epoxide generation by dimethyldioxirane oxidation and the use of epichlorohydrin in the flow synthesis of a library of β-amino alcohols.

Authors:  Peter J Cossar; Jennifer R Baker; Nicholas Cain; Adam McCluskey
Journal:  R Soc Open Sci       Date:  2018-04-04       Impact factor: 2.963

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