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.
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收藏
页码：31 / 35
页数：5
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