Copper-Catalyzed Intramolecular Aldehyde–Ketone Nucleophilic Additions for the Synthesis of Chromans Bearing a Tertiary Alcohol Motif

The synthesis of chroman-3-ol derivatives via intramolecular nucleophilic additions has been established. Aldehydes can be used as alkyl carbanion equivalents via reductive polarity reversal which is facilitated by a copper catalyst and N-heterocyclic carbene ligand under mild conditions. The key to...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 89; no. 2; pp. 1220 - 1227
Main Authors Zhu, Chenghao, Jiang, Wenbo, Ma, Da
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.01.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
TRIAZOLIUM SALTS
ASYMMETRIC-SYNTHESIS
FACILE SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
ACID CATALYSIS
CONSTRUCTION
STETTER REACTION
BENZOIN
DYNAMIC KINETIC RESOLUTION
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Summary:The synthesis of chroman-3-ol derivatives via intramolecular nucleophilic additions has been established. Aldehydes can be used as alkyl carbanion equivalents via reductive polarity reversal which is facilitated by a copper catalyst and N-heterocyclic carbene ligand under mild conditions. The key to success is the difference in reaction activity between aldehydes and ketones. Finally, this methodology also can be used to construct other cyclic structures containing tertiary alcohols including tetraline, cyclohexane, indan, and 9,10-dihydrophenanthrene.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02365