Dehydrative Reduction:  A Highly Diastereoselective Synthesis of syn-Bisaryl(or Heteroaryl) Dihydrobenzoxathiins and Benzodioxane

TFA/Et3SiH-mediated cyclization of thioketones 5 derived from the reaction of functionalized thiophenols (catechols) with bromo ketones gave syn 2,3-bisaryl(or heteroaryl) dihydrobenzoxathiins and benzodioxane 1 with total diastereoselectivity (>99:1), in excellent yields.

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Bibliographic Details
Published inOrganic letters Vol. 5; no. 5; pp. 685 - 688
Main Authors Kim, Seongkon, Wu, Jane Y, Chen, Helen Y, DiNinno, Frank
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 06.03.2003
Subjects
Catechols - chemistry
Cyclization
Dioxanes - chemical synthesis
Ketones - chemistry
Oxidation-Reduction
Stereoisomerism
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Summary:TFA/Et3SiH-mediated cyclization of thioketones 5 derived from the reaction of functionalized thiophenols (catechols) with bromo ketones gave syn 2,3-bisaryl(or heteroaryl) dihydrobenzoxathiins and benzodioxane 1 with total diastereoselectivity (>99:1), in excellent yields.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol0274763