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Efficient asymmetric TADDOLs-organocatalyzed cycloaddition for the synthesis of allyltin derivatives

Paper ID Volume ID Publish Year Pages File Format Full-Text
49934 46773 2015 6 PDF Available
Title
Efficient asymmetric TADDOLs-organocatalyzed cycloaddition for the synthesis of allyltin derivatives
Abstract

•Efficient organocatalytic asymmetric Diels–Alder reactions were studied in this work.•Stereo defined allyltin derivatives synthesized with excellent yields.•Excellent regio- and endoselectivity achieved.•TADDOL and TADDOL derivatives used as very efficient organocatalysts.

We report here the results obtained in the study of organocatalytic asymmetric Diels–Alder reactions to optimize the synthesis of stereo defined allyltin derivatives using (Z)-2-(1-cyclohexenyl)-1-ethenyl(trineophyl)stannane (1) as diene and substituted dienophiles in the presence of (4R,5R)-α,α,α′,α′-tetraphenyl-1,3-dioxolane-4,5-dimethanol (TADDOL, I) and analogs (4R,5R)-α,α,α′,α′-tetra(1-naphtyl)-1,3-dioxolane-4,5-dimethanol (II) and (4R,5R)-α,α,α′,α′-tetra(9-phenantryl)1,3-dioxolane-4,5-dimethanol (III) as chiral catalysts to enhance stereoselectivity through hydrogen bond activation of the dienophile. Catalyst II provided excellent results and ultrasonic radiation at low temperature showed the shorter reaction times.

Keywords
Asymmetric organocatalysis; TADDOLs; Diels–Alder; Reaction; Allyltin derivatives
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Efficient asymmetric TADDOLs-organocatalyzed cycloaddition for the synthesis of allyltin derivatives
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 58, 5 January 2015, Pages 209–214
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us