Stereoselective synthesis of (1R,4R)-N-acyl-2-oxa-5-aza-bicyclo[2.2.1]heptan-3-ones via mesoionic compounds. An improved synthesis of cis-4-hydroxy-d-proline

Autor:	Concetta La Rosa, Piero Dalla Croce
Rok vydání:	2002
Předmět:	Bicyclic molecule Chemistry Stereochemistry Organic Chemistry Enantioselective synthesis Mesoionic Cleavage (embryo) Catalysis Inorganic Chemistry Acetic anhydride chemistry.chemical_compound Stereoselectivity Proline Physical and Theoretical Chemistry
Zdroj:	Tetrahedron: Asymmetry. 13:197-201
ISSN:	0957-4166
DOI:	10.1016/s0957-4166(02)00074-5
Popis:	We report an asymmetric synthesis of (1 R ,4 R )- N -acyl-2-oxa-5-aza-bicyclo[2.2.1]heptan-3-ones, starting from the inexpensive and commercially available trans -4-hydroxy- l -proline and achieved by treating N -acyl- trans -4-hydroxy- l -prolines with acetic anhydride. The formation of intermediate mesoionic compounds may explain the formation of N -acyl-2-oxa-5-aza-bicyclo[2.2.1]heptan-3-ones with ( R )-absolute configuration at C(4). Acidic cleavage of these lactones readily affords N -acyl- cis -4-hydroxy- d -prolines or cis -4-hydroxy- d -proline in good yields.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::d151843fb0a8dda85f39c0e6353e1bfd https://doi.org/10.1016/s0957-4166(02)00074-5 Zobrazit plný text záznamu Full Text from ScienceDirect