Regioselective Base‐Promoted Nucleophilic Ring Opening of Spirocyclic 2,6‐Dioxopiperazines: Synthesis of  N ‐(1‐Carboxycyclohexyl)amino Acid Derivatives | Zendy

GonzálezVera Juan A. | Zendy; GarcíaLópez M. Teresa | Zendy; Herranz Rosario | Zendy

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Regioselective Base‐Promoted Nucleophilic Ring Opening of Spirocyclic 2,6‐Dioxopiperazines: Synthesis of N ‐(1‐Carboxycyclohexyl)amino Acid Derivatives

Author(s) -

GonzálezVera Juan A.,

GarcíaLópez M. Teresa,

Herranz Rosario

Publication year - 2007

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200600714

Subject(s) - chemistry , regioselectivity , nucleophile , ring (chemistry) , nucleophilic addition , imide , base (topology) , hydroxide , medicinal chemistry , amino acid , stereochemistry , organic chemistry , catalysis , mathematical analysis , biochemistry , mathematics

Amino acid derived spirocyclic 2,6‐dioxopiperazines are easily and regioselectively opened by base‐promoted nucleophilic attack of hydroxide or H 2 O on the less crowded carbonyl group at C‐6 to give N ‐(1‐carbamoylcyclohexyl)amino acid derivatives. However, the imide group of the 2,6‐dioxopiperazine ring is rather unreactive toward alcohols, alkoxides, and amines. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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