Literature DB >> 24377351

Asymmetric radical addition of TEMPO to titanium enolates.

Phillip J Mabe1, Armen Zakarian.   

Abstract

A mild method for α-hydroxylation of N-acyl oxazolidinones by asymmetric radical addition of the 2,2,6,6-tetramethylpiperidine N-oxy (TEMPO) radical to titanium enolates was developed. The high diastereoselectivity and broad scope of the reaction show synthetic utility for the α-hydroxylation of substrates that are not tolerant to strongly basic conditions.

Entities:  

Year:  2013        PMID： 24377351     DOI： 10.1021/ol403398u

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


  5 in total

1.  Evans Enolates: Solution Structures of Lithiated Oxazolidinone-Derived Enolates.

Authors:  Evan H Tallmadge; David B Collum
Journal:  J Am Chem Soc       Date:  2015-10-05       Impact factor: 15.419

2.  Structures and Reactivities of Sodiated Evans Enolates: Role of Solvation and Mixed Aggregation on the Stereochemistry and Mechanism of Alkylations.

Authors:  Zirong Zhang; David B Collum
Journal:  J Am Chem Soc       Date:  2018-12-17       Impact factor: 15.419

3.  Stereoselective α-Tertiary Alkylation of N-(Arylacetyl)oxazolidinones.

Authors:  Eunjae Shim; Armen Zakarian
Journal:  Synlett       Date:  2020-04       Impact factor: 2.454

4.  Hydrative Aminoxylation of Ynamides: One Reaction, Two Mechanisms.

Authors:  Alexandre Pinto; Daniel Kaiser; Boris Maryasin; Giovanni Di Mauro; Leticia González; Nuno Maulide
Journal:  Chemistry       Date:  2018-01-24       Impact factor: 5.236

5.  A Photocatalytic System Composed of Benzimidazolium Aryloxide and Tetramethylpiperidine 1-Oxyl to Promote Desulfonylative α-Oxyamination Reactions of α-Sulfonylketones.

Authors:  Tsukasa Tanaka; Takehiro Kiuchi; Yuuki Ooe; Hajime Iwamoto; Shin-Ya Takizawa; Shigeru Murata; Eietsu Hasegawa
Journal:  ACS Omega       Date:  2022-01-26
  5 in total

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