Asymmetric Synthesis of Conformationally Constrained trans-2,3-Piperidinedicarboxylic Acid Derivatives

Autor:	Costas Agrios, Brian Metcalf, Lingkai Weng, Ding-Quan Qian, David M. Burns, Yun-Long Li, Jincong Zhuo, Colin Zhang, Meizhong Xu, Qiyan Lin, Chunhong He, Eric Shi, Wenqing Yao
Rok vydání:	2007
Předmět:	Olefin fiber Chemistry Cyclopropanation Stereochemistry Organic Chemistry Aspartic acid Intramolecular cyclization Enantioselective synthesis Stereoselectivity
Zdroj:	Synlett. 2007:0460-0464
ISSN:	1437-2096 0936-5214
DOI:	10.1055/s-2007-968029
Popis:	An efficient asymmetric synthesis of conformationally constrained (2S,3S)-piperidinedicarboxylic acid derivatives starting from L-aspartic acid β-tert-butyl ester and 3-chloro-2-(chloromethyl)-1-propene is described. The key steps involve N-alkylation of the aspartic acid ester followed by a stereoselective enolate intramolecular cyclization (>95:5 dr). Various synthetic strategies were explored to achieve the cyclopropanation of the resulting olefin, including the Simmons-Smith reaction and palladium-catalyzed cyclopropanation.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::8ecff296c2c3f79070f2e572b0dd7cac https://doi.org/10.1055/s-2007-968029 Zobrazit plný text záznamu