- Total selective synthesis of enantiopure O1-acyl-3-aminoalkane- 1,2-diols by ring opening of aminoepoxides with carboxylic acids
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Synthesis of (2R,3S)- or (2S,3S)-O1-acyl-3-aminoalkane-1,2-diols by ring opening of enantiopure (2R,1′S)- or (2S,1′S)-2-(1- aminoalkyl)epoxides 1 or 2, with carboxylic acids in the presence of BF 3·Et2O and chlorotrimethyl
- Concellon, Jose M.,Suarez, Jose Ramon,Del Solar, Virginia,Llavona, Ricardo
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p. 10348 - 10353
(2007/10/03)
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- Highly Diastereoselective Synthesis of Threo or Erythro Aminoalkyl Epoxides from α-Amino Acids
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α-Chloro-α'-(dibenzylamino)methylketones 3 are synthesized in enantiomerically pure form starting from α-amino acids.Reduction of amino ketones 3 and further epoxidation affords threo aminoalkyl epoxides 6 with diastereoisomeric excess ranging between 94percent and 98percent.The synthesis of erythro amino epoxides 9 is also described by reaction of α-amino aldehydes 7 with in situ generated (halomethyl)lithium.Amino epoxides 9 were obtained with a diastereoisomeric excess ranging between 91percent and 98percent.
- Barluenga, Jose,Baragana, Beatriz,Concellon, Jose M.
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p. 6696 - 6699
(2007/10/03)
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