Regio- and Diastereodivergent [4 + 2] Cycloadditions
with Cyclic 2,4‑Dienones
Posted on 2017-12-14 - 17:51
By 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.
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Xiao, Wei; Yang, Qian-Qian; Chen, Zhi; Ouyang, Qin; Du, Wei; Chen, Ying-Chun (2017). Regio- and Diastereodivergent [4 + 2] Cycloadditions
with Cyclic 2,4‑Dienones. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b03598
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AUTHORS (6)
WX
Wei Xiao
QY
Qian-Qian Yang
ZC
Zhi Chen
QO
Qin Ouyang
WD
Wei Du
YC
Ying-Chun Chen