کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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5223917 | 1383502 | 2008 | 9 صفحه PDF | دانلود رایگان |
The behaviour towards the retro-aldol or retro-Dieckmann reactions of several norbornene and norbornane amino acids functionalized with an oxygen atom at C-β and characterized by different features, such as the substitution pattern and the constraints, was investigated. By C2-C3 disconnection new differently functionalized cyclopentenyl- and cyclopentylglycines were prepared. This synthetic approach allows to control the stereochemistry from two to four stereocentres depending on the starting norbornane derivative and affords, for each derivative, a couple of epimeric compounds at amino acid stereocentre. Depending on the features of the starting reagent and of the reaction conditions, a partial control of the stereochemistry of the amino acid carbon atom is also possible.
Journal: Tetrahedron - Volume 64, Issue 24, 9 June 2008, Pages 5657-5665