TY - JOUR
T1 - Organocatalytic Enantioselective 1,3-Dipolar [6+4] Cycloadditions of Tropone
AU - Bertuzzi, Giulio
AU - McLeod, David
AU - Mohr, Lisa Marie
AU - Jørgensen, Karl Anker
PY - 2020/12
Y1 - 2020/12
N2 - A highly stereoselective 1,3-dipolar [6+4] cycloaddition towards bridged azabicyclo[4.3.1]decane scaffolds has been developed, reacting aldehydes, 2-aminomalonates and tropone under mild conditions in the presence of a chiral phosphoric acid catalyst. The scope is demonstrated for a series of aldehydes and 2-aminomalonates, and the reaction proceeds in high yields, >95:5 d.r. and up to 99 % ee. A series of transformations, as well as a mechanistic proposal, are presented.
AB - A highly stereoselective 1,3-dipolar [6+4] cycloaddition towards bridged azabicyclo[4.3.1]decane scaffolds has been developed, reacting aldehydes, 2-aminomalonates and tropone under mild conditions in the presence of a chiral phosphoric acid catalyst. The scope is demonstrated for a series of aldehydes and 2-aminomalonates, and the reaction proceeds in high yields, >95:5 d.r. and up to 99 % ee. A series of transformations, as well as a mechanistic proposal, are presented.
KW - 1,3-dipole
KW - chiral phosphoric acids
KW - enantioselectivity
KW - higher-order cycloadditions
KW - tropone
UR - http://www.scopus.com/inward/record.url?scp=85092686527&partnerID=8YFLogxK
U2 - 10.1002/chem.202003329
DO - 10.1002/chem.202003329
M3 - Journal article
C2 - 32677710
AN - SCOPUS:85092686527
SN - 0947-6539
VL - 26
SP - 15491
EP - 15496
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 67
ER -