Structural analysis of three methyl N-phosphorylated 5,6-dihydroxy-2-azabicyclo[2.2.1]heptane-3-carboxylates

• Type: Article in International Scientific Journal
• Date: 2012

Authors

Carlos A D Sousa (Author) Other; Luisa L C Vale (Author) FCUP; Jose E Rodriguez Borges (Author) FCUP; Xerardo Garcia Mera (Author) Other

Journal

Title: Journal of Molecular Structure

Vol. 1007

Pages: 31-35

ISSN: 0022-2860

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 2 Citations

Scopus - 2 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-002-DY5

DOI: 10.1016/j.molstruc.2011.09.041

Abstract (EN): Both exo and endo isomers of (+/-)-methyl N-diphenylphosphoryl-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate and (+/-)-methyl N-diphenylphosphoryloxy-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate were dihydroxylated with OsO4. The unexpected formation of (+/-)-methyl 5,6-dihydroxy-N-diphenylphosphoryl-2-azabicyclo[2.2.1]heptane-3-endo-carboxylate from (+/-)-methyl N-diphenylphosphoryloxy-2-azabicyclo[2.2.1]hept-5-ene-3-endo-carboxylate is discussed based on NMR analyses and experimental observations. The two N-diphenylphosphoryl dihydroxybicycles are analyzed in terms of their crystalline structure by X-ray crystallography.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 5