高级α-氯代乙烯基和α-溴代乙烯基氨基酸的合成：氨基保护基团决定反应进程。
Synthesis of Higher α-Chlorovinyl and α-Bromovinyl Amino Acids: The Amino Protecting Group Determines the Reaction Course.
作者信息
Berkowitz David B, Pedersen Michelle L, Jahng Wan-Jin
机构信息
Department of Chemistry, University of Nebraska-Lincoln, Lincoln, NE 68588-0304.
出版信息
Tetrahedron Lett. 1996 Jun 17;37(25):4309-4312. doi: 10.1016/0040-4039(96)00832-5.
Abstract
N-Trifluoroacetyl α-vinyl amino esters are smoothly converted to the corresponding α-chlorovinyl or α-bromovinyl amino esters through the agency of phenyselenyl chloride or phenylselenyl bromide, respectively, followed by oxidation and pyrolysis. Exclusively the (E)-extemal halovinyl isomer and the internal halovinyl isomer are observed. The amino protecting group is a critical determinant of the reaction course (alkene addition vs. 5-exo-trig-like cyclization).
摘要
通过苯硒基氯或苯硒基溴的作用，N-三氟乙酰基α-乙烯基氨基酯分别顺利地转化为相应的α-氯代乙烯基或α-溴代乙烯基氨基酯，随后进行氧化和热解。仅观察到（E）-外卤代乙烯基异构体和内卤代乙烯基异构体。氨基保护基是反应历程（烯烃加成与5-外环化反应）的关键决定因素。
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