Phosphoric Acid Catalyzed Aldehyde Addition to in Situ Generated o‑Quinone Methides: An Enantio- and Diastereoselective Entry toward cis-3,4-Diaryl Dihydrocoumarins

A highly stereoselective, phosphoric acid catalyzed synthesis of cis-3,4-diarylchromanols through reaction of o-hydroxybenzhydryl alcohols and aryl acetaldehydes is reported. The products can be further manipulated to 3,4-dihydrocoumarins, 4H-chromenes, and chromanes with good overall yields and ver...

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Bibliographic Details
Published inOrganic letters Vol. 20; no. 16; pp. 4769 - 4772
Main Authors Spanka, Matthias, Schneider, Christoph
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.08.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BRONSTED ACID
ACTIVATION
ASYMMETRIC-SYNTHESIS
ANTIFERTILITY AGENTS
ENANTIOSELECTIVE SYNTHESIS
ANNULATION
CYCLOADDITIONS
DIELS-ALDER REACTION
BETA-DICARBONYLS
BRANCHED CYCLIC-KETONES
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Summary:A highly stereoselective, phosphoric acid catalyzed synthesis of cis-3,4-diarylchromanols through reaction of o-hydroxybenzhydryl alcohols and aryl acetaldehydes is reported. The products can be further manipulated to 3,4-dihydrocoumarins, 4H-chromenes, and chromanes with good overall yields and very good diastereo- and enantiocontrol. This reaction is based upon the concept of enol catalysis and comprises the in situ generation of hydrogen-bonded o-quinone methides and their formal [4 + 2]-cycloaddition with aldehyde enols.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b01865