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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.