Stereoselective Synthesis of Spiro Bis-C,C-α-arylglycosides by Tandem Heck Type C‑Glycosylation and Friedel–Crafts Cyclization

Spiro bis-C,C-α-arylglycosides were synthesized in three steps in 78–85% overall yields starting from exo-glycals. The initial Heck type C-aryl addition of exo-glycals with arylboronic acids afforded α-aryl-β-substituted C-glycosides with exclusive α-stereoselectivity. Among the products, β-ethanal...

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Published inJournal of organic chemistry Vol. 81; no. 7; pp. 3007 - 3016
Main Authors Chen, Yen-Bo, Liu, Shi-Hao, Hsieh, Min-Tsang, Chang, Chih-Shiang, Lin, Chun-Hung, Chen, Chen-Yin, Chen, Po-Yen, Lin, Hui-Chang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.04.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PALLADIUM
POTENT
FACILE SYNTHESIS
REAGENTS
ANALOGS
CATALYZED COUPLING REACTION
ORGANIC HALIDES
GLYCOSIDE SYNTHESIS
ARYLBORONIC ACIDS
EXO-GLYCALS
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Summary:Spiro bis-C,C-α-arylglycosides were synthesized in three steps in 78–85% overall yields starting from exo-glycals. The initial Heck type C-aryl addition of exo-glycals with arylboronic acids afforded α-aryl-β-substituted C-glycosides with exclusive α-stereoselectivity. Among the products, β-ethanal α-aryl C-glycosides further reacted with alkylthiol in the presence of InCl3, followed by in situ Friedel–Crafts cyclization to yield the desirable final products. We proposed a mechanism to explain how the α-aryl group serves as a main determinant of the cyclization.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b02891