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 | Zendy

Zhu ChengZhi | Zendy; Wei Yin | Zendy; Shi Min | Zendy

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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.

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