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A facile synthesis of optically pure L-armentomycin and its D-isomer.Highly enantioselective reduction of the CC double bond of methyl (E)- and (Z)-2,4,4-trichloro-2-butenoate by using baker's yeast

✍ Scribed by Masanori Utaka; Satoshi Konishi; Toshiyasu Okubo; Sadao Tsuboi; Akira Takeda


Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
192 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis


Optically pure L-armentomycin t(S)-2-amino-4,4-dichlorobutanoic acid] and its D-isomer [(R)-2-amino-4,4-dichlorobutanoic acid] were prepared by using methyl (E)-and (Z)-2,4,4-trichloro-2-butenoate as key intermediate, which were reduced with baker's yeast to (R)-and (S)-2,4,4-trichlorobutanoate in 84-92 and 97-98% ee, respectively, in 60-65% yields.