Preparation of Bicyclic Ketal Skeletons with Aldehyde and alpha-Ketone Acid through Cascade Friedel-Crafts Reaction and Stereoselective Acetalization in One Pot

Bicyclic ketal skeletons are important structure fragments that are frequently contained in natural products. A novel tandem Friedel-Crafts reaction and subsequent stereoselective acetalization were developed with readily available aldehyde and ketone acid. The reaction proceeded smoothly in the pre...

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Bibliographic Details
Published inSynlett Vol. 30; no. 18; pp. 2091 - 2095
Main Authors Li, Ling, Wang, Ying-wei, Zhang, Shi-qi, Dong, Xiong-fei, Li, Guang-xun, Zhao, Gang, Tang, Zhuo
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 12.11.2019
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
tandem reaction
Bronsted acid
TANDEM
PRODUCTS
bicyclic ketal skeletons
alpha-ketone acid
acetalization
CARBONYL-COMPOUNDS
SINGLET OXYGEN
Friedel-Crafts reaction
RHODIUM CARBENOIDS
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Summary:Bicyclic ketal skeletons are important structure fragments that are frequently contained in natural products. A novel tandem Friedel-Crafts reaction and subsequent stereoselective acetalization were developed with readily available aldehyde and ketone acid. The reaction proceeded smoothly in the presence of catalytic Bronsted acid and afforded the corresponding product with moderate yield and high stereoselectivity.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0039-1690696