Literature DB >> 24138164

A simple, scalable synthetic route to (+)- and (-)-pseudoephenamine.

Kevin T Mellem1, Andrew G Myers.   

Abstract

A three-step synthesis of pseudoephenamine suitable for preparing multigram amounts of both enantiomers of the auxiliary from the inexpensive starting material benzil is described. The sequence involves synthesis of the crystalline monomethylimine derivative of benzil, reduction of that substance with lithium aluminum hydride, and resolution of pseudoephenamine with mandelic acid.

Entities:  

Mesh：

Substances：

Year:  2013        PMID： 24138164      PMCID： PMC3864801          DOI： 10.1021/ol402815d

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


  5 in total

1.  Stereoselective Reduction of Benzils: A New Convenient Route to Enantiomerically Pure 1,2-Diarylethanediols.

Authors:  K. R. K. Prasad; N. N. Joshi
Journal:  J Org Chem       Date:  1996-05-31       Impact factor: 4.354

2.  Synthesis of quaternary α-methyl α-amino acids by asymmetric alkylation of pseudoephenamine alaninamide pivaldimine.

Authors:  Cedric L Hugelshofer; Kevin T Mellem; Andrew G Myers
Journal:  Org Lett       Date:  2013-06-07       Impact factor: 6.005

3.  Pseudoephenamine: a practical chiral auxiliary for asymmetric synthesis.

Authors:  Marvin R Morales; Kevin T Mellem; Andrew G Myers
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-27       Impact factor: 15.336

4.  Oxo-tethered ruthenium(II) complex as a bifunctional catalyst for asymmetric transfer hydrogenation and H2 hydrogenation.

Authors:  Taichiro Touge; Tomohiko Hakamata; Hideki Nara; Tohru Kobayashi; Noboru Sayo; Takao Saito; Yoshihito Kayaki; Takao Ikariya
Journal:  J Am Chem Soc       Date:  2011-08-31       Impact factor: 15.419

5.  A concise and versatile double-cyclization strategy for the highly stereoselective synthesis and arylative dimerization of Aspidosperma alkaloids.

Authors:  Jonathan William Medley; Mohammad Movassaghi
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-12       Impact factor: 15.336
  5 in total
  3 in total

1.  Disodium Salts of Pseudoephedrine-Derived Myers Enolates: Stereoselectivity and Mechanism of Alkylation.

Authors:  Yuhui Zhou; Ivan Keresztes; Samantha N MacMillan; David B Collum
Journal:  J Am Chem Soc       Date:  2019-10-15       Impact factor: 15.419

2.  Enantioselective Construction of Acyclic Quaternary Carbon Stereocenters: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Amide Enolates.

Authors:  Pavel Starkov; Jared T Moore; Douglas C Duquette; Brian M Stoltz; Ilan Marek
Journal:  J Am Chem Soc       Date:  2017-07-07       Impact factor: 15.419

3.  Stereocontrolled synthesis of syn-β-Hydroxy-α-amino acids by direct aldolization of pseudoephenamine glycinamide.

Authors:  Ian B Seiple; Jaron A M Mercer; Robin J Sussman; Ziyang Zhang; Andrew G Myers
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-01       Impact factor: 15.336
  3 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.