Trienamine Catalysis with 2,4-Dienones: Development and Application in Asymmetric Diels-Alder Reaction

TY - JOUR

T1 - Trienamine Catalysis with 2,4-Dienones: Development and Application in Asymmetric Diels-Alder Reaction

AU - Xiong, Xiaofeng

AU - Chen, Ying-Chun

AU - Gu, Jing

PY - 2012/4/27

Y1 - 2012/4/27

N2 - A tri-ing reaction: An asymmetric Diels-Alder cycloaddition of δ,δ-disubstituted 2,4-dienones is possible through the trienamine catalysis of cinchona-based primary amines (see scheme). An array of electron-deficient dienophiles, such as N-substituted maleimides and 3-alkenyl oxindoles, were tolerated, and multifunctional cyclohexene derivatives were obtained in excellent stereoselectivity and with high diastereomer ratios.

AB - A tri-ing reaction: An asymmetric Diels-Alder cycloaddition of δ,δ-disubstituted 2,4-dienones is possible through the trienamine catalysis of cinchona-based primary amines (see scheme). An array of electron-deficient dienophiles, such as N-substituted maleimides and 3-alkenyl oxindoles, were tolerated, and multifunctional cyclohexene derivatives were obtained in excellent stereoselectivity and with high diastereomer ratios.

M3 - Letter

SN - 1433-7851

VL - 51

SP - 4401

EP - 4402

JO - Angewandte Chemie, Int. Ed.

JF - Angewandte Chemie, Int. Ed.

ER -