Direct Synthesis of 6‐Azabicyclo[3.2.1]oct‐6‐en‐2‐ones and Pyrrolizidines from Divinyl Ketones and Observation of Remarkable Substituent Effects | Zendy

Xu Xianxiu | Zendy; Li Yifei | Zendy; Zhang Yu | Zendy; Zhang Lingjuan | Zendy; Pan Ling | Zendy; Liu Qun | Zendy

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Direct Synthesis of 6‐Azabicyclo[3.2.1]oct‐6‐en‐2‐ones and Pyrrolizidines from Divinyl Ketones and Observation of Remarkable Substituent Effects

Author(s) -

Xu Xianxiu,

Li Yifei,

Zhang Yu,

Zhang Lingjuan,

Pan Ling,

Liu Qun

Publication year - 2011

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.201000880

Subject(s) - chemistry , substituent , alkyl , aryl , ketone , group (periodic table) , stereochemistry , medicinal chemistry , organic chemistry

Substituents create access to molecular diversity. Under basic conditions, 6‐azabicyclo[3.2.1]oct‐6‐en‐2‐ones 3 and pyrrolizidines 4 are efficiently synthesized, respectively, in a single step from ethyl isocyanoacetate 2 and divinyl ketones 1 bearing an aryl or alkyl group at the 2‐position. For comparison, only the corresponding pyrrolizidines 4 ′ can be obtained from divinyl ketones 1 ′ bearing a methoxycarbonyl group at the 2‐position.

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