Concise synthesis of (+)-allo-kainic acid via MgI2-mediated tandem aziridine ring opening-formal [3 + 2] cycloaddition

Autor:	Daniele Leonori, Giada Arena, Varinder K. Aggarwal, Chia-Chun Chen
Rok vydání:	2013
Předmět:	Kainic acid Pyrrolidines Vinyl Compounds Stereochemistry Aziridines CHIRAL NITRIDOMANGANESE COMPLEX 010402 general chemistry Ring (chemistry) 01 natural sciences Biochemistry chemistry.chemical_compound ACTIVATED OLEFINS Alloys Physical and Theoretical Chemistry ENE-TYPE REACTIONS ASYMMETRIC-SYNTHESIS ENANTIOSELECTIVE SYNTHESIS Kainic Acid Tandem Cycloaddition Reaction Molecular Structure (+/-)-ALPHA-ALLOKAINIC ACID 010405 organic chemistry Organic Chemistry KAINIC ACID Enantioselective synthesis Stereoisomerism CATALYZED CASCADE REACTIONS Aziridine EXCITATORY AMINO-ACIDS Cycloaddition 0104 chemical sciences chemistry Cyclization SN2 reaction Alpha-allokainic acid HIGHLY SUBSTITUTED PYRROLIDINES
Zdroj:	Arena, G, Chen, C-C, Leonori, D & Aggarwal, V K 2013, ' Concise Synthesis of (+)-allo-Kainic Acid via MgI2-Mediated Tandem Aziridine Ring Opening-Formal [3+2] Cycloaddition ', Organic Letters, vol. 15, no. 16, pp. 4250-4253 . https://doi.org/10.1021/ol4020333
ISSN:	1523-7052
Popis:	3-Methyl vinyl aziridine undergoes a mild MgI2-promoted S(N)2' ring opening and concomitant cyclization with fumarate Michael acceptors to give trisubstituted pyrrolidines. The process is efficient and highly diastereoselective. This methodology has been applied to a concise asymmetric synthesis of (+)-allo-kainic acid.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::a6def1916aba75e001f01c3e8d6e88b6 https://pubmed.ncbi.nlm.nih.gov/23909824 Zobrazit plný text záznamu