Catalytic Dearomative Spirocyclization via Gold Carbene Species Derived from Ynamides: Efficient Synthesis of 2‐Azaspiro[4.5]decan‐3‐ones

Catalytic Dearomative Spirocyclization via Gold Carbene Species Derived from Ynamides: Efficient... An intramolecular catalytic dearomatization of phenols via gold carbene species proceeded to provide 2‐azaspiro[4.5]decan‐3‐ones. The use of NHC ligand and water as a co‐solvent was critical for achieving high reactivity. This reaction did not require hazardous diazo compounds as carbene sources and proceeded even under air. The obtained spirocyclic product could be readily transformed into a gabapentin derivative by hydrogenation and deprotection. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Chemistry - A European Journal Wiley

Catalytic Dearomative Spirocyclization via Gold Carbene Species Derived from Ynamides: Efficient Synthesis of 2‐Azaspiro[4.5]decan‐3‐ones

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Publisher
Wiley Subscription Services, Inc., A Wiley Company
Copyright
© 2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
0947-6539
eISSN
1521-3765
D.O.I.
10.1002/chem.201800314
Publisher site
See Article on Publisher Site

Abstract

An intramolecular catalytic dearomatization of phenols via gold carbene species proceeded to provide 2‐azaspiro[4.5]decan‐3‐ones. The use of NHC ligand and water as a co‐solvent was critical for achieving high reactivity. This reaction did not require hazardous diazo compounds as carbene sources and proceeded even under air. The obtained spirocyclic product could be readily transformed into a gabapentin derivative by hydrogenation and deprotection.

Journal

Chemistry - A European JournalWiley

Published: Jan 12, 2018

Keywords: ; ; ; ;

References

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