High Diastereoselective Synthesis of Threo or Erythro Aminoalkyl Epoxides from. alpha.-Amino Acids
J Barluenga, B Baragana… - The Journal of Organic …, 1995 - ACS Publications
J Barluenga, B Baragana, JM Concellon
The Journal of Organic Chemistry, 1995•ACS Publicationsa-Chloro-a'-(dibenzylamino) methylketones 3 are synthesized in enantiomerically pure form
starting from-amino acids. Reduction of amino ketones 3 and further epoxidation affords
threo aminoalkyl epoxides 6 with diastereoisomeric excess ranging between 94% and 98%.
The synthesis of erythro amino epoxides 9 is also described by reaction of-amino aldehydes
7 with in situ generated (halomethyl) lithium. Amino epoxides 9 were obtained with a
diastereoisomeric excess ranging between 91% and 98%.
starting from-amino acids. Reduction of amino ketones 3 and further epoxidation affords
threo aminoalkyl epoxides 6 with diastereoisomeric excess ranging between 94% and 98%.
The synthesis of erythro amino epoxides 9 is also described by reaction of-amino aldehydes
7 with in situ generated (halomethyl) lithium. Amino epoxides 9 were obtained with a
diastereoisomeric excess ranging between 91% and 98%.
a-Chloro-a'-(dibenzylamino) methylketones 3 are synthesized in enantiomerically pure form starting from-amino acids. Reduction of amino ketones 3 and further epoxidation affords threo aminoalkyl epoxides 6 with diastereoisomeric excess ranging between 94% and 98%. The synthesis of erythro amino epoxides 9 is also described by reaction of-amino aldehydes 7 with in situ generated (halomethyl) lithium. Amino epoxides 9 were obtained with a diastereoisomeric excess ranging between 91% and 98%.
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