Literature DB >> 15646952

A general method for the preparation of N-sulfonyl aldimines and ketimines.

José Luis García Ruano1, José Alemán, M Belén Cid, Alejandro Parra.   

Abstract

[Reaction: see text] A simple procedure to obtain N-sulfonyl imines involving the condensation of carbonyl compounds with p-tolyl or tert-butyl sulfinamides followed by oxidation with m-CPBA of the resulting N-sulfinylimines is reported. The method is applicable to aldehydes (aliphatics and aromatics) and ketones (diaryl, dialkyl, and aryl alkyl), even those containing enolizable protons. It also does not affect C=N or C=C double bonds and does not epimerize alpha-stereogenic centers.

Entities:  

Year:  2005        PMID: 15646952     DOI: 10.1021/ol048005e

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


  6 in total

1.  Synthesis-guided structure revision of the sarcodonin, sarcoviolin, and hydnellin natural product family.

Authors:  David W Lin; Takeshi Masuda; Moritz B Biskup; Jonathan D Nelson; Phil S Baran
Journal:  J Org Chem       Date:  2011-01-20       Impact factor: 4.354

2.  Synthesis of polysubstituted pyrroles from sulfinimines (N-sulfinyl imines).

Authors:  Franklin A Davis; Kerisha A Bowen; He Xu; Venkata Velvadapu
Journal:  Tetrahedron       Date:  2008-05-05       Impact factor: 2.457

3.  Asymmetric synthesis of syn-propargylamines and unsaturated β-amino acids under Brønsted base catalysis.

Authors:  Yingcheng Wang; Mingjie Mo; Kongxi Zhu; Chao Zheng; Hongbin Zhang; Wei Wang; Zhihui Shao
Journal:  Nat Commun       Date:  2015-10-01       Impact factor: 14.919

4.  Practical N-Hydroxyphthalimide-Mediated Oxidation of Sulfonamides to N-Sulfonylimines.

Authors:  Jian Wang; Wen-Jing Yi
Journal:  Molecules       Date:  2019-10-19       Impact factor: 4.411

5.  Synthesis of cis-C-iodo-N-tosyl-aziridines using diiodomethyllithium: reaction optimization, product scope and stability, and a protocol for selection of stationary phase for chromatography.

Authors:  Tom Boultwood; Dominic P Affron; Aaron D Trowbridge; James A Bull
Journal:  J Org Chem       Date:  2013-06-18       Impact factor: 4.354

6.  Sulfinamide Synthesis Using Organometallic Reagents, DABSO, and Amines.

Authors:  Pui Kin Tony Lo; Gwyndaf A Oliver; Michael C Willis
Journal:  J Org Chem       Date:  2020-04-14       Impact factor: 4.354

  6 in total

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