Literature DB >> 18275212

Remarkable salt effect on In-mediated allylation of N-tert-butanesulfinyl imines in aqueous media: highly practical asymmetric synthesis of chiral homoallylic amines and isoindolinones.

Xing-Wen Sun1, Min Liu, Ming-Hua Xu, Guo-Qiang Lin.   

Abstract

A highly practical and efficient asymmetric synthesis of chiral homoallylic amines by In-mediated allylation of chiral N-tert-butanesulfinyl imines in aqueous media at room temperature was developed. With 2-formylbenzoate imine substrates, the method allows the highly enantioselective achievement of a variety of pharmacologically important 3-allyl isoindolinone compounds.

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Year:  2008        PMID： 18275212     DOI： 10.1021/ol8001514

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


  9 in total

1.  Highly diastereoselective and general synthesis of primary β-fluoroamines.

Authors:  Michael L Schulte; Craig W Lindsley
Journal:  Org Lett       Date:  2011-09-26       Impact factor: 6.005

2.  A versatile enantioselective synthesis of azabicyclic ring systems: a concise total synthesis of (+)-grandisine D and unnatural analogues.

Authors:  Olugbeminiyi O Fadeyi; Timothy J Senter; Kristopher N Hahn; Craig W Lindsley
Journal:  Chemistry       Date:  2012-03-30       Impact factor: 5.236

3.  Enantioselective synthesis of homoallylic amines through reactions of (pinacolato)allylborons with aryl-, heteroaryl-, alkyl-, or alkene-substituted aldimines catalyzed by chiral C1-symmetric NHC-Cu complexes.

Authors:  Erika M Vieira; Marc L Snapper; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2011-02-22       Impact factor: 15.419

4.  Synthesis and Biological Evaluation of Cremastrine and an Unnatural Analogue.

Authors:  Kristopher N Hahn; Olugbeminiyi O Fadeyi; Hyekyung P Cho; Craig W Lindsley
Journal:  Tetrahedron Lett       Date:  2012-05-10       Impact factor: 2.415

5.  Asymmetric Petasis Borono-Mannich Allylation Reactions Catalyzed by Chiral Biphenols.

Authors:  Yao Jiang; Scott E Schaus
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-04       Impact factor: 15.336

6.  Synthesis and Optimization of Nitroxide-Based Inhibitors of Ferroptotic Cell Death in Cancer Cells and Macrophages.

Authors:  Manwika Charaschanya; Taber S Maskrey; Matthew G LaPorte; Jelena M Janjic; Peter Wipf
Journal:  ACS Med Chem Lett       Date:  2022-02-04       Impact factor: 4.345

7.  A General, Enantioselective Synthesis of 1-Azabicyclo[m.n.0]alkane Ring Systems.

Authors:  Timothy J Senter; Michael L Schulte; Leah C Konkol; Tyler E Wadzinski; Craig W Lindsley
Journal:  Tetrahedron Lett       Date:  2013-03-27       Impact factor: 2.415

8.  Preparation of Enantiomerically Pure Perfluorobutanesulfinamide and Its Application to the Asymmetric Synthesis of α-Amino Acids.

Authors:  Apiwat Wangweerawong; Joshua R Hummel; Robert G Bergman; Jonathan A Ellman
Journal:  J Org Chem       Date:  2016-02-04       Impact factor: 4.354

9.  Rigid and concave, 2,4-cis-substituted azetidine derivatives: A platform for asymmetric catalysis.

Authors:  Akina Yoshizawa; Antonio Feula; Louise Male; Andrew G Leach; John S Fossey
Journal:  Sci Rep       Date:  2018-04-25       Impact factor: 4.379
  9 in total

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