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Synthesis and Ring Opening of Methyl 2‐Alkyl‐3‐(alkyl/aryl)‐1‐benzoylaziridine‐2‐carboxylates: Synthesis of Polysubstituted Amino Acids
Author(s) -
Papa Carmela,
Tomasini Claudia
Publication year - 2000
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/(sici)1099-0690(200004)2000:8<1569::aid-ejoc1569>3.0.co;2-x
Subject(s) - chemistry , alkyl , aziridine , ring (chemistry) , amino acid , aryl , lithium (medication) , organic chemistry , medicinal chemistry , medicine , biochemistry , endocrinology
A new method for the preparation of 2,2,3‐trisubstituted methyl 1‐benzoylaziridine‐2‐carboxylates is reported. These compounds have been obtained starting from α‐alkyl β‐amino acids by formation of the lithium dianion and reaction with iodine. The aziridines undergo ring expansion or ring opening, depending on the substituents of the aziridine ring and on the reaction conditions. Following these methods, both α‐substituted α‐hydroxy β‐amino acids and α‐substituted β‐hydroxy α‐amino acids have been synthesised.