TY - JOUR
T1 - Diene-Transmissive Enantioselective Diels-Alder Reactions and Sequences Involving Substituted Dendralenes
AU - George, Josemon
AU - Sherburn, Michael S.
N1 - Publisher Copyright:
Copyright © 2019 American Chemical Society.
PY - 2019/11/15
Y1 - 2019/11/15
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85074580081&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.9b02296
DO - 10.1021/acs.joc.9b02296
M3 - Article
SN - 0022-3263
VL - 84
SP - 14712
EP - 14723
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 22
ER -