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

被引：2

作者：

Sousa, Carlos A. D. ^{[1
]}

Vale, M. Luisa C. ^{[1
]}

Rodriguez-Borges, Jose E. ^{[1
]}

Garcia-Mera, Xerardo ^{[2
]}

机构：

[1] Univ Porto, Fac Ciencias, Dept Quim & Bioquim, Ctr Invest Quim, P-4169007 Oporto, Portugal

[2] Univ Santiago de Compostela, Fac Farm, Dept Quim Organ, E-15782 Santiago De Compostela, Spain

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2012年 / 1007卷

关键词：

Hydroxylation; Azabicyclo[2.2.1]hept-5-enes; Phosphoryl group; X-ray; NMR; ROUTE;

D O I：

10.1016/j.molstruc.2011.09.041

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

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. (C) 2011 Elsevier B.V. All rights reserved.

引用

页码：31 / 35

页数：5