Regioselective S<sub>N</sub>2' Mitsunobu reaction of Morita–Baylis–Hillman alcohols: A facile and stereoselective synthesis of α-alkylidene-β-hydrazino acid derivatives

Xu, Silong; Shang, Jian Ku; Zhang, Junjie; Tang, Yuhai

doi:10.3762/bjoc.10.98

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2015

2023

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Cited by 6 publications

References 48 publications

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A Diastereoselective Route to trans‐2‐Aryl‐2,3‐dihydrobenzofurans through Sequential Cross‐Metathesis/Isomerization/Allylboration Reactions: Synthesis of Bioactive Neolignans

2015

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The structure of a nickel complex of imidazoline–aminophenol (IAP) prepared from IAP with Ni(OAc)2 was elucidated as cis‐bis(imidazolineaminophenoxide) [Ni(IAP)2]. The [Ni(IAP)2] complex smoothly promoted catalytic asymmetric 1,4‐addition of 3′‐indolyl‐3‐oxindole to nitroethylene to provide chiral mixed 3,3′‐bisindoles with high enantioselectivities. Mechanistic studies using ESI‐MS analyses suggest that one IAP ligand dissociated from [Ni(IAP)2] to generate the Ni–enolate of 3′‐indolyl‐3‐oxindole. From the optically active 3,3′‐mixed indole adduct, biologically important 3′‐indolyl‐3‐pyrrolidinoindoline was successfully synthesized in a three‐step reaction sequence.

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