Stereocontrolled synthesis of alpha,alpha-disubstituted alpha-aminoaldehydes and alpha-aminoacids using a [3,3] allylic trichloracetimidate rearrangement
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作者:
Imogai, H
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ECOLE NORMALE SUPER,CNRS,ORGAN SYNTH LAB,F-75231 PARIS 05,FRANCEECOLE NORMALE SUPER,CNRS,ORGAN SYNTH LAB,F-75231 PARIS 05,FRANCE
Imogai, H
[1
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Petit, Y
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ECOLE NORMALE SUPER,CNRS,ORGAN SYNTH LAB,F-75231 PARIS 05,FRANCEECOLE NORMALE SUPER,CNRS,ORGAN SYNTH LAB,F-75231 PARIS 05,FRANCE
Petit, Y
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Larcheveque, M
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ECOLE NORMALE SUPER,CNRS,ORGAN SYNTH LAB,F-75231 PARIS 05,FRANCEECOLE NORMALE SUPER,CNRS,ORGAN SYNTH LAB,F-75231 PARIS 05,FRANCE
Larcheveque, M
[1
]
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[1] ECOLE NORMALE SUPER,CNRS,ORGAN SYNTH LAB,F-75231 PARIS 05,FRANCE
Sigmatropic rearrangement of trichloracetimidates derived from syn monoprotected allylic diols 3 resulting from the condensation of vinylalanes or cuprates with alpha-alkoxyaldehydes afforded diastereomerically pure allylic amines 6. The oxidative cleavage of these amines allowed the access to alpha,alpha-disubstituted alpha-aminoacids in high enantiomeric purity. Copyright (C) 1996 Published by Elsevier Science Ltd