Ring opening reactions of cyclic sulfamidates. Synthesis of β-fluoroaryl alanines and derivatives of 4,4-difluoroglutamic acid
Ring opening reactions of cyclic sulfamidates. Synthesis of β-fluoroaryl alanines and derivatives of 4,4-difluoroglutamic acid
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DOI：
10.1016/j.jfluchem.2018.11.003
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发表时间：
2019-01-01
影响因子：
1.9
通讯作者：
Ignatowska, Jolanta
中科院分区：
文献类型：
--
作者：
Bolek, Sylwia;Ignatowska, Jolanta
1与Cu、TMEDA和BrCF 2CO 2 Et之间形成的铜络合物的开环反应以中等产率产生光学活性的4，4-二氟谷氨酸衍生物11 a-d。环磺酰胺酯1与氟取代的芳基氯化镁的反应通过铜催化的格氏试剂与原位形成的脱氢丙氨酸2的1，4-加成进行。无论反应条件如何，氟化的有机锌衍生物对1都不反应;相反，分离出1与DMF的反应产物。
Ring opening reactions of 1 with copper complex formed between Cu, TMEDA and BrCF2CO2Et lead to optically active 4,4-difluoroglutamic acid derivatives 11a-d in moderate yields. Reaction of cyclic sulfamidates 1 with fluoro substituted arylmagnesium chlorides proceed via copper catalyzed 1,4-addition of Grignard reagent to dehydroalanine 2, formed in situ. Fluorinated organoznic derivatives were unreactive towards 1 regardless of the reaction conditions; instead product of reaction of 1 with DMF was isolated.