化学
废止
合成子
磷化氢
酰亚胺
电泳剂
钋
催化作用
亚甲基
药物化学
有机化学
有机催化
组合化学
对映选择合成
作者
Zhibing Zhang,Zhenkai Zhang,Yuhao Wang,Bo-Ting Chen,Fengkai He,Yi Long Wang,Tao Shu,Yiyong Huang
标识
DOI:10.1021/acs.joc.4c00388
摘要
The trivalent phosphine-catalyzed [4+1] spiro-annulation reaction of allenyl imide and activated methylene cyclocompounds has been developed for the construction of various spiro-2-cyclopenten-1-ones. Oxindoles, 3-isochromanones, and 2-indanones are selected as 1C synthons to capture the in situ-generated bis-electrophilic α,β-unsaturated ketenyl phosphonium intermediate, affording the corresponding monospiro- and bispiro-cyclopentenones in good to excellent yields (≤91%) under mild conditions. The primary attempt at asymmetric catalysis using monophosphine (R)-SITCP provides promising enantioselectivity (45% ee). A plausible reaction mechanism is also proposed.
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