Literature DB >> 21469662

Enantiopure 1,4-diols and 1,4-aminoalcohols via stereoselective acyclic sulfoxide-sulfenate rearrangement.

Roberto Fernández de la Pradilla1, Ignacio Colomer, Mercedes Ureña, Alma Viso.   

Abstract

Treatment of acyclic α-hydroxy and α-tosylamino sulfinyl dienes with amines affords enantiopure 1,4-diol or 1,4-hydroxysulfonamide derivatives in good yields and diastereoselectivities. This one-pot procedure entails a conjugate addition that triggers a diastereoselective sulfoxide-sulfenate [2,3]-sigmatropic rearrangement.

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Year:  2011        PMID: 21469662     DOI: 10.1021/ol200718y

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


  2 in total

1.  Selective Radical-Radical Cross-Couplings: Design of a Formal β-Mannich Reaction.

Authors:  Jenna L Jeffrey; Filip R Petronijević; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2015-06-29       Impact factor: 15.419

2.  Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

Authors:  Daniel Kaiser; Immo Klose; Rik Oost; James Neuhaus; Nuno Maulide
Journal:  Chem Rev       Date:  2019-06-25       Impact factor: 60.622

  2 in total

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