Literature DB >> 11009380

Yb(OTf)(3)-Catalyzed oxymercuration of homoallylic alcohol-derived hemiacetals and hemiketals.

S D Dreher1, K R Hornberger, S T Sarraf, J L Leighton.   

Abstract

1,3-Diol synthons, protected as acetonides or benzylidene acetals, may be synthesized efficiently from homoallylic alcohols and acetone or benzaldehyde by oxymercuration of the derived hemiketals and hemiacetals with HgClOAc. The use of catalytic amounts of Yb(OTf)(3) is crucial to the success of the reaction, which was determined to be reversible.

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Year:  2000        PMID: 11009380     DOI: 10.1021/ol0063860

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


  2 in total

1.  Dynamic kinetic resolution of transient hemiketals: a strategy for the desymmetrisation of prochiral oxetanols.

Authors:  Alexander Sandvoß; Henning Maag; Constantin G Daniliuc; Dieter Schollmeyer; Johannes M Wahl
Journal:  Chem Sci       Date:  2022-05-04       Impact factor: 9.969

2.  Trapping Hemiacetals with Phosphono Substituted Palladium π-Allyl Complexes for the Synthesis of Substituted Cyclic Ethers.

Authors:  Nongnuch Sutivisedsak; Surendra Dawadi; Christopher D Spilling
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

  2 in total

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