ol7b03598_si_001.pdf (12.26 MB)
Regio- and Diastereodivergent [4 + 2] Cycloadditions with Cyclic 2,4‑Dienones
journal contribution
posted on 2017-12-14, 17:51 authored by Wei Xiao, Qian-Qian Yang, Zhi Chen, Qin Ouyang, Wei Du, Ying-Chun ChenBy employing activated
alkenes with bulky α-functional groups,
such as α-cyano-α,β-unsaturated ketones and Meldrum’s
acid–based alkenes, a previously unreported cross-trienamine
pathway of cyclic 2,4-dienones is adopted to deliver γ′,δ-regioselective
[4 + 2] cycloadducts catalyzed by cinchona-derived amines. In addition,
a diastereodivergent [4 + 2] cycloaddition reaction is realized with Z-configured 4-alkylideneisoxazol-5(4H)-ones under similar catalytic conditions, even through a three-
or four-component cascade process with simple starting materials.