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本文引用的文献

1
Enantiomerically Enriched α-Methyl Amino Acids. Use of an Acyclic, Chiral Alanine-Derived Dianion with a High Diastereofacial Bias.对映体富集的α-甲基氨基酸。使用具有高非对映面选择性的无环手性丙氨酸衍生双负离子。
J Org Chem. 1995 Mar;60(5):1233-1238. doi: 10.1021/jo00110a029.
2
Free α-Oxiranyl Amino Acids.游离α-环氧乙烷基氨基酸。
J Org Chem. 1995 Sep;60(17):5368-5369. doi: 10.1021/jo00122a002.
3
Inhibition of tryptophan synthase by (1-fluorovinyl)glycine.（1-氟乙烯基）甘氨酸对色氨酸合酶的抑制作用。
Biochemistry. 1993 Jan 26;32(3):806-11. doi: 10.1021/bi00054a010.
4
Synthesis and evaluation of mono-, di-, and trifluoroethenyl-GABA derivatives as GABA-T inhibitors.单氟乙烯基、二氟乙烯基和三氟乙烯基 -γ-氨基丁酸衍生物作为γ-氨基丁酸转氨酶抑制剂的合成与评价
J Med Chem. 1987 Feb;30(2):267-72. doi: 10.1021/jm00385a007.
5
Antibacterial activities of fluorovinyl- and chlorovinylglycine and several derived dipeptides.氟乙烯基甘氨酸和氯乙烯基甘氨酸以及几种衍生二肽的抗菌活性。
Antimicrob Agents Chemother. 1988 Mar;32(3):319-23. doi: 10.1128/AAC.32.3.319.
6
Mechanism-based inactivation of alanine racemase by 3-halovinylglycines.3-卤代乙烯基甘氨酸对丙氨酸消旋酶的基于机制的失活作用。
J Biol Chem. 1991 Nov 15;266(32):21657-65.

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.

DOI:10.1016/0040-4039(96)00832-5
PMID:29200438
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5708561/
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。