Diene-Transmissive Enantioselective Diels-Alder Reactions and Sequences Involving Substituted Dendralenes
Date
2019
Authors
Sherburn, Michael
George, Josemon
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American Chemical Society
Abstract
Readily available and stable substituted [3]-
dendralenes undergo highly chemo-, regio-, diastereo-, and
enantioselective organocatalyzed Diels−Alder reactions with
acrolein to form enantiomerically enriched cycloadducts.
These monocycloadducts carry semicyclic dienes that undergo
a second, substrate-controlled diastereoselective Diels−Alder
reaction with a different dienophile to form 2-fold cycloadducts. Overall, annulated, functional group rich, chiral Δ1(9)-
octalin building blocks are accessed in one-pot operations that
significantly extend the preparative value of diene-transmissive Diels−Alder sequences since they offer products of regio- and
stereochemistry complementary to those generated from the parent, unsubstituted [3]dendralene
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Journal of Organic Chemistry
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Journal article
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2037-12-31
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