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Tetrahedron. 2001 Jul 23;57(30):6329-6343. doi: 10.1016/S0040-4020(01)00499-9.
2
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3
Synthesis of quaternary amino acids bearing a (2'Z)-fluorovinyl alpha-branch: potential PLP enzyme inactivators.带有(2'Z)-氟乙烯基α-支链的季铵氨基酸的合成：潜在的磷酸吡哆醛（PLP）酶失活剂
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Engineering acyclic stereocontrol in the alkylation of vinylglycine-derived dianions: asymmetric synthesis of higher alpha-vinyl amino acids.乙烯基甘氨酸衍生二价阴离子烷基化反应中的无环立体控制：高级α-乙烯基氨基酸的不对称合成
J Org Chem. 2000 May 19;65(10):2907-18. doi: 10.1021/jo9918091.
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Cu(I)/Rh(II)-Catalyzed Tandem Convergent Multicomponent Reaction for the Regio- and Stereocontrolled Synthesis of γ-Oxo-β-amino Esters.Cu(I)/Rh(II)-催化的串联会聚多组分反应用于 γ-氧代-β-氨基酯的区域和立体选择性合成。
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Palladium-catalyzed insertion of alpha-diazoesters into vinyl halides to generate alpha,beta-unsaturated gamma-amino esters.钯催化α-重氮酯插入卤代乙烯中生成α,β-不饱和γ-氨基酯。
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Total Synthesis of the Sensitive Triyne Natural Product (4,5)-4,8-Dihydroxy-3,4-dihydrovernoniyne and All of Its Stereoisomers.（4,5）-4,8-二羟基-3,4-二氢 vernoniyne 及其全部立体异构体的敏感三炔天然产物的全合成。
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Synthesis and Deployment of an Elusive Fluorovinyl Cation Equivalent: Access to Quaternary α-(1'-Fluoro)vinyl Amino Acids as Potential PLP Enzyme Inactivators.合成和部署难以捉摸的氟乙烯基阳离子等价物：获得潜在的 PLP 酶失活剂作为四元α-（1'-氟）乙烯基氨基酸。
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A useful methoxyvinyl cation equivalent: α-t-butyldimethylsilyl-α-methoxyacetaldehyde.一种有用的甲氧基乙烯基阳离子等价物：α-叔丁基二甲基硅烷基-α-甲氧基乙醛。
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A formal [3,3]-sigmatropic rearrangement route to quaternary alpha-vinyl amino acids: use of allylic N-PMP trifluoroacetimidates.通往季碳α-乙烯基氨基酸的一种形式上的[3,3] - 迁移重排途径：烯丙基N - PMP三氟乙酰亚胺酯的应用。
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Synthesis of quaternary amino acids bearing a (2'Z)-fluorovinyl alpha-branch: potential PLP enzyme inactivators.带有(2'Z)-氟乙烯基α-支链的季铵氨基酸的合成：潜在的磷酸吡哆醛（PLP）酶失活剂
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本文引用的文献

1
Organoselenium-Based Entry into Versatile, α-(2-Tributylstannyl)vinyl Amino Acids in Scalemic Form: A New Route to Vinyl Stannanes.基于有机硒的手性α-(2-三丁基锡基)乙烯基氨基酸的合成：乙烯基锡烷的新合成路线。
J Am Chem Soc. 2000 Nov 8;122(44):11031-11032. doi: 10.1021/ja0055110. Epub 2000 Oct 21.
2
A Convenient Synthesis of L-α-Vinylglycine from L-Homoserine Lactone.由L-高丝氨酸内酯便捷合成L-α-乙烯基甘氨酸
Synthesis (Stuttg). 1996 Jan;1996(1):39-41. doi: 10.1055/s-1996-4177.
3
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.
4
Synthesis of Higher α-Chlorovinyl and α-Bromovinyl Amino Acids: The Amino Protecting Group Determines the Reaction Course.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。
Tetrahedron Lett. 1996 Jun 17;37(25):4309-4312. doi: 10.1016/0040-4039(96)00832-5.
5
α-VINYLLYSINE AND α-VINYLARGININE ARE TIME-DEPENDENT INHIBITORS OF THEIR COGNATE DECARBOXYLASES.α-乙烯基赖氨酸和α-乙烯基精氨酸是其同源脱羧酶的时间依赖性抑制剂。
Bioorg Med Chem Lett. 1996 Sep 17;6(18):2151-2156. doi: 10.1016/0960-894X(96)00366-6.
6
The Stille Reaction of 1,1-Dibromo-1-alkenes: Preparation of Trisubstituted Alkenes and Internal Alkynes.1,1-二溴-1-烯烃的施蒂勒反应：三取代烯烃和内炔烃的制备
J Org Chem. 1999 Nov 26;64(24):8873-8879. doi: 10.1021/jo991116k.
7
Preparation and Synthetic Applications of (S)- and (R)-N-Boc-N,O-isopropylidene-alpha-methylserinals: Asymmetric Synthesis of (S)- and (R)-2-Amino-2-methylbutanoic Acids (Iva).（S）-和（R）-N-叔丁氧羰基-N，O-异亚丙基-α-甲基丝氨酸的制备及其合成应用：（S）-和（R）-2-氨基-2-甲基丁酸（Iva）的不对称合成
J Org Chem. 1999 Oct 29;64(22):8220-8225. doi: 10.1021/jo990957o.
8
Et(2)AlCl-Catalyzed Cyclization of Epoxytrichloroacetimidates for the Synthesis of alpha-Substituted Serines.Et(2)AlCl催化环氧三氯乙酰亚胺酯环化反应合成α-取代丝氨酸
J Org Chem. 1997 Apr 4;62(7):2275-2279. doi: 10.1021/jo9618278.
9
Synthesis of (S)-alpha-cyclopropyl-4-phosphonophenylglycine.（S）-α-环丙基-4-膦酰基苯甘氨酸的合成
J Org Chem. 2001 Jan 12;66(1):348-50. doi: 10.1021/jo0013711.
10
The first water-soluble 3(10)-helical peptides.首批水溶性3(10)-螺旋肽。
Chemistry. 2000 Dec 15;6(24):4498-504. doi: 10.1002/1521-3765(20001215)6:24<4498::aid-chem4498>3.0.co;2-4.

季碳β,γ-不饱和氨基酸的立体控制合成：D-和L-α-(2-三丁基锡烷基)乙烯基氨基酸的链增长

Stereocontrolled Synthesis of Quaternary β,γ-Unsaturated Amino Acids: Chain Extension of D- & L- α-(2-Tributylstannyl)Vinyl Amino Acids.

作者信息

Berkowitz David B, Chisowa Esmort, McFadden Jill M

机构信息

Department of Chemistry, University of Nebraska, Lincoln, NE 68588-0304.

出版信息

Tetrahedron. 2001 Jul 23;57(30):6329-6343. doi: 10.1016/S0040-4020(01)00499-9.

DOI:10.1016/S0040-4020(01)00499-9
PMID:29973743
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6027620/
Abstract

A pair of diastereomeric (4S,5S)- and (4S,5R)-4-methoxycarbonyl-5-phenylselenomethyl-2-phenyl oxazolines, derived from L-vinylglycine, serve as precursors to protected, quaternary, L- and D-α-(2-tributylstannyl)vinyl amino acids, respectively, in three steps {(i) alkylative side chain installation, (ii) eliminative ring-opening and (iii) vinyl selenide to vinyl stannane interconversion}. The title compounds may be protodestannylated to the corresponding free, quaternary L- and D-vinyl amino acids. Alternatively, the 2-stannylvinyl α-branch (or the derivative 2-iodovinyl branch) may be exploited to access novel quaternary, L- and D-β,γ-unsaturated amino acids via a range of transition metal-mediated cross coupling reactions.

摘要

一对由L-乙烯基甘氨酸衍生而来的非对映异构的(4S,5S)-和(4S,5R)-4-甲氧基羰基-5-苯基硒甲基-2-苯基恶唑啉，分别作为受保护的季铵型L-和D-α-(2-三丁基锡基)乙烯基氨基酸的前体，反应分三步进行{(i) 烷基化侧链安装，(ii) 消除开环和(iii) 乙烯基硒化物到乙烯基锡烷的相互转化}。标题化合物可脱锡生成相应的游离季铵型L-和D-乙烯基氨基酸。或者，2-锡基乙烯基α-支链（或衍生物2-碘乙烯基支链）可用于通过一系列过渡金属介导的交叉偶联反应获得新型季铵型L-和D-β,γ-不饱和氨基酸。