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Rhodium(II)‐Catalyzed Intramolecular Transannulation of 4‐Methoxycyclohexa‐2,5‐dienone Tethered 1‐Sulfonyl‐1,2,3‐triazoles: Synthesis of Azaspiro[5.5]undecane Derivatives
Author(s) -
Zhu ChengZhi,
Wei Yin,
Shi Min
Publication year - 2019
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.201900290
Subject(s) - chemistry , intramolecular force , oxonium ion , rhodium , sulfonyl , ylide , carbene , undecane , catalysis , medicinal chemistry , stereochemistry , organic chemistry , ion , alkyl
A Rh(II)‐catalyzed denitrogenative intramolecular transannulation using 4‐methoxycyclohexa‐2,5‐dienone tethered N ‐sulfonyl‐1,2,3‐triazoles as substrates has been developed, affording diversified 3‐methoxy‐1‐tosyl‐1‐azaspiro[5.5]undecanes in moderate to good yields under mild conditions. This new synthetic method proceeded through an oxonium ylide generated from trapping a rhodium(II)‐carbene by methoxy group, a methoxy group migration, and C−N bond formation, providing an interesting synthetic strategy for the construction of spirocyclic frameworks.