TY - JOUR
T1 - Multicomponent Diene-Transmissive Diels-Alder Sequences Featuring Aminodendralenes
AU - Tan, Siu Min
AU - Willis, Anthony C.
AU - Paddon-Row, Michael N.
AU - Sherburn, Michael S.
N1 - Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
PY - 2016/2/24
Y1 - 2016/2/24
N2 - 1-Aminodecalins were prepared from acyclic precursors by combining the powerful twofold diene-transmissive Diels-Alder chemistry of [3]dendralenes with the simplicity of enamine formation. On mixing at ambient temperature, a simple dienal condenses with a primary or secondary amine to generate the enamine, a 1-amino-[3]dendralene in situ, and this participates as a double diene in a sequence of two Diels-Alder events with separate dienophiles. Overall, four C-C bonds and one C-N bond are formed. Mechanistic insights into these reactions are provided by means of density functional theory calculations.
AB - 1-Aminodecalins were prepared from acyclic precursors by combining the powerful twofold diene-transmissive Diels-Alder chemistry of [3]dendralenes with the simplicity of enamine formation. On mixing at ambient temperature, a simple dienal condenses with a primary or secondary amine to generate the enamine, a 1-amino-[3]dendralene in situ, and this participates as a double diene in a sequence of two Diels-Alder events with separate dienophiles. Overall, four C-C bonds and one C-N bond are formed. Mechanistic insights into these reactions are provided by means of density functional theory calculations.
KW - Diels-Alder reactions
KW - density functional calculations
KW - domino reactions
KW - multicomponent reactions
KW - polycycles
UR - http://www.scopus.com/inward/record.url?scp=84959497571&partnerID=8YFLogxK
U2 - 10.1002/anie.201510925
DO - 10.1002/anie.201510925
M3 - Article
SN - 1433-7851
VL - 55
SP - 3081
EP - 3085
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 9
ER -