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Generalized Approach to Asymmetric Synthesis of β‐Substituted β‐Amino Acids Bearing CHF 2 , CBrF 2 , and CClF 2 Groups
Author(s) -
Dai Yanling,
Xie Chen,
Zhou Jie,
Mei Haibo,
Soloshonok Vadim A.,
Han Jianlin,
Pan Yi
Publication year - 2015
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500252
Subject(s) - chemistry , amino acid , alkyl , combinatorial chemistry , molecule , organic chemistry , biological activity , fluorine , bearing (navigation) , biochemistry , in vitro , cartography , geography
Currently, there is a great demand for the development of new methods for the preparation of fluorine containing compounds. However, biologically relevant molecules bearing fluoroalkyl groups other than CF 3 still remain virtually unexplored. Herein, we report a simple approach for preparation of β‐amino acids derivatives containing CHF 2 , CBrF 2 , and CClF 2 groups via addition reactions of the corresponding ( S s)‐ N ‐( tert ‐butanesulfinyl)‐CXF 2 ‐acetaldimines and alkyl‐acetate‐derived enolates. The reactions occur with excellent diastereoselectivity of up to >99:1 providing a simple and reliable access to a type of biologically valuable derivatives.