New spirocyclic oxindole synthesis based on a hetero Claisen rearrangement

Organic Letters
Zhan Mao, Steven W Baldwin

Abstract

[reaction: see text] A new method for preparing spirocyclic oxindoles is presented. Featuring a [3,3]-sigmatropic enolate rearrangement, the three-step process converts carboxylic acid starting materials to oxidnole products in overall yields of 52-76%. The enolate rearrangement step occurs at -78 degrees C and provides easy access to oxindole products that have previously been difficult to prepare.

References

Mar 30, 1977·Journal of the American Chemical Society·C Stinson, P Hambright

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Citations

Sep 1, 2015·Organic Letters·Xiangyang FengWeiqing Xie
Sep 18, 2009·Chemistry : a European Journal·Géraldine RousseauYannick Landais
Sep 12, 2008·Organic Letters·Géraldine RousseauYannick Landais
Aug 4, 2009·Organic Letters·Nicolas DuguetAndrew D Smith
Sep 20, 2019·The Journal of Organic Chemistry·Jing Zhang, Fu-She Han
May 16, 2012·Organic Letters·Edward RichmondAndrew D Smith
Jun 27, 2013·Organic Letters·Heng-Yen Wang, Laura L Anderson
Mar 19, 2014·Chemical Reviews·Andrey A Tabolin, Sema L Ioffe

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