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参考文献:Chiral Electrophilic "glycinal" Equivalents. New Synthons For Optically Active α-Amino Acids And 4-Substituted 2-Oxazolidinones
标题:Chiral Electrophilic "glycinal" Equivalents. New Synthons For Optically Active α-Amino Acids And 4-Substituted 2-Oxazolidinones
摘要:The Thermal Reaction Of 3-[(Is)-2-Alkoxy-1-Apocamphanecarbonyl]-2-Oxazolones (21A-C) With Dialkyl Azodicarboxylates (9) Results In Exclusive Formation Of [4 + 2] Type Cycloadducts (22 And 23) With Moderate Levels Of Diastereofacial Selection (Up To 72% D.E.). The Diastereomers Thus Obtained Were Readily Purified And Subsequent Treatment With Acidic Methanol Followed By Removal Of The Auxiliary With Libh4/meoh (1:2) Gave Optically Pure 4-Methoxy-5-Hydrazino-2-Oxazolidinones (26 And 27),Which Serve As Alpha-Aminoaldehyde Templates Useful For The Synthesis Of A Wide Variety Of Optically Active Alpha-Amino Acids As Well As 4-Alkyl And 4-Aryl-2-Oxazolidinones. (C) 1997,Elsevier Science Ltd.
Doi:10.1016/s0040-4020(96)01077-0