Synthesis of Bicyclic Pyroglutamic Acid Featuring the Ugi Reaction and a Unique Stereoisomerization at the Angular Position by Grob Fragmentation Followed by a Transannular Ketene [2+2] Cycloaddition Reaction

Synthesis of Bicyclic Pyroglutamic Acid Featuring the Ugi Reaction and a Unique Stereoisomerization at the Angular Position by Grob Fragmentation Followed by a Transannular Ketene [2+2] Cycloaddition Reaction

Abstract A stereoisomerization at the angular position of N-acylindoles during basic hydrolysis was discovered to give only the SYN-bicyclic pyroglutamic acid, proceeding through a transannular [2+2] cycloaddition of a ketene-ketone intermediate generated by a Grob fragmentation.

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Veröffentlicht in:Synlett 2007-06, Vol.2007 (10), p.1595-1599
Hauptverfasser: Vamos, Mitchell, Ozboya, Kerem, Kobayashi, Yoshihisa
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container_title Synlett
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creator Vamos, Mitchell
Ozboya, Kerem
Kobayashi, Yoshihisa
description Abstract A stereoisomerization at the angular position of N-acylindoles during basic hydrolysis was discovered to give only the SYN-bicyclic pyroglutamic acid, proceeding through a transannular [2+2] cycloaddition of a ketene-ketone intermediate generated by a Grob fragmentation.
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title Synthesis of Bicyclic Pyroglutamic Acid Featuring the Ugi Reaction and a Unique Stereoisomerization at the Angular Position by Grob Fragmentation Followed by a Transannular Ketene [2+2] Cycloaddition Reaction
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