One‐Pot Synthesis of Cyclopropanes from Methylene Azabicyclo[3.1.0]hexanes Obtained by Formal Sequential [1+2]‐ and [2+3]‐Cycloaddition Reaction of Prop‐2‐ynylsulfonium Salts and Tosylaminomethyl Enones | Zendy

Jia Penghao | Zendy; Zhang Qinglong | Zendy; Zhuge Yuzhou | Zendy; Liwei Xingyue | Zendy; Huang You | Zendy

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One‐Pot Synthesis of Cyclopropanes from Methylene Azabicyclo[3.1.0]hexanes Obtained by Formal Sequential [1+2]‐ and [2+3]‐Cycloaddition Reaction of Prop‐2‐ynylsulfonium Salts and Tosylaminomethyl Enones

Author(s) -

Jia Penghao,

Zhang Qinglong,

Zhuge Yuzhou,

Liwei Xingyue,

Huang You

Publication year - 2018

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.201700959

Subject(s) - chemistry , synthon , annulation , enamine , methylene , cycloaddition , hexane , medicinal chemistry , organic chemistry , combinatorial chemistry , catalysis

A formal sequential [1+2]‐ and [2+3]‐annulation of prop‐2‐ynylsulfonium salts and tosylaminomethyl enones was developed, constructing a series of methylene azabicyclo[3.1.0]hexane derivatives. A one‐pot procedure was established via hydration of an enamine intermediate to afford substituted cyclopropanes. Prop‐2‐ynylsulfonium salts acted as both C 2 and C 1 synthons in these two processes.

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