SCHEDULED MAINTENANCE
A highly efficient method to access unprotected C-3 bifunctional quaternary 3-allyl-3-(amino)oxindoles†
Xunbo
Lu, 
*a
Guoling
Huang,
‡a
*a
Guoling
Huang,
‡a
Abstract
A highly efficient Rh(II) catalyzed non-radical protocol to access NH-free C-3 bifunctional oxindoles, which possess 3-allyl and 3-amino simultaneously, was first achieved by employing an intermolecular [2,3]-sigmatropic rearrangement reaction between diazooxindoles and tertiary allylic amines. Utilizing readily available allylamines as the nitrogen and allyl source concurrently, a wide range of bio-active 3-allyl-3-(amino)oxindoles were obtained in excellent yields under very mild reaction conditions; meanwhile, the TON can be up to 90 000. Our study addresses a gap in the literature by investigating intermolecular rearrangements of ammonium ylides with diazoamides, which have been relatively understudied.
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