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Biocatalytic Synthesis of Enantiopure β‐Methoxy‐β‐arylalanine Derivatives
Author(s) -
Fan Shiming,
Liu Shouxin,
Zhang Hubo,
Liu Ying,
Yang Yihuang,
Jin Longyi
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402470
Subject(s) - chemistry , enantiopure drug , diastereomer , catalysis , resolution (logic) , organic chemistry , base (topology) , stereochemistry , enantioselective synthesis , mathematical analysis , mathematics , artificial intelligence , computer science
Chiral β‐hydroxy‐β‐arylalanine and β‐methoxy‐β‐arylalanine derivatives, which occur widely in marine nature products, were stereoselectively synthesized with 99 % ee values. The two erythro isomers were prepared by L ‐ or D ‐aminoacylase‐catalyzed resolution of the corresponding N ‐acetyl derivatives, whereas the two threo isomers were obtained only by D ‐aminoacylase‐catalyzed resolution of the derivatives. erythro ‐β‐Hydroxy‐β‐arylalanine derivatives were prepared by diastereoselective hydrogenation of ethyl 2‐(hydroxyimino)‐3‐oxo‐3‐arylpropanoates, which were in turn acquired by the oximation of ethyl 3‐oxo‐3‐arylpropanoates with ethyl nitrite in the presence of nano‐K 2 CO 3 with yields of 72 % to 80 %. β‐Methoxy‐β‐arylalanine derivatives were synthesized through Williamson reactions between the corresponding β‐hydroxy‐β‐arylalanines and iodomethane with silver oxide as base.