A novel, high-yielding approach to a chiral inducer: (2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diol

A new method for preparing (2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diol in high yield based on selective 2,3-spiroboration of (2R,3R)-1,1,4,4-tetraphenylbutanetetraol has been developed. It avoids traditional oxidation and reduction steps, and provides a simplified, more straightforward,...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 25; no. 6-7; pp. 503 - 506
Main Authors Hu, Xiaoyun, Shan, Zixing, Song, Shaojun
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.04.2014
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
REAGENT
ALCOHOLS
BINOL
ASYMMETRIC-SYNTHESIS
(2R,3R)-1,4-DIMETHOXY-1,1,4,4-TETRAPHENYL-2,3-BUTANEDIOL
ACIDS
ALDEHYDES
DERIVATIVES
TADDOLS
PURE ALLYLBORONIC ESTERS
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Summary:A new method for preparing (2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diol in high yield based on selective 2,3-spiroboration of (2R,3R)-1,1,4,4-tetraphenylbutanetetraol has been developed. It avoids traditional oxidation and reduction steps, and provides a simplified, more straightforward, and high-yielding synthesis of the title compound.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2014.01.018