A rapid approach to amino-acid derivatives by [2,3]-Stevens rearrangement

被引：0

作者：

Arboré, APA ^{[1
]}

Cane-Honeysett, DJ ^{[1
]}

Coldham, I ^{[1
]}

Middleton, ML ^{[1
]}

机构：

[1] Univ Exeter, Sch Chem, Exeter EX4 4QD, Devon, England

来源：

SYNLETT | 2000年 / 02期

关键词：

amines; amino acids; rearrangements; ylides; chirality transfer;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allylation of amino-acid esters gives rise to intermediate quaternary ammonium salts, which undergo proton abstraction to give ylides and [2,3]-sigmatropic rearrangement. The resulting alpha-amino-acid derivatives can be subjected to N-deallylation to provide a rapid access to alpha-allyl-alpha-amino-esters. Using N-benzyl proline methyl ester, chirality transfer from carbon to nitrogen then back to carbon takes place.

引用

页码：236 / 238

页数：3

共 50 条

[31] Synthesis of amino-acid derivatives of chrysin
Veselovskaya, M. V.
Garazd, M. M.
Ogorodniichuk, A. S.
Garazd, Ya. L.
Khilya, V. P.
CHEMISTRY OF NATURAL COMPOUNDS, 2008, 44 (06) : 704 - 711
[32] DERIVATIVES FOR SEPARATION OF AMINO-ACID ENANTIOMERS
ABDALLA, S
BAYER, E
FRANK, H
CHROMATOGRAPHIA, 1987, 23 (02) : 83 - 85
[33] ENZYMATIC AMMONIOLYSIS OF AMINO-ACID DERIVATIVES
DEZOETE, MC
OUWEHAND, AA
VANRANTWIJK, F
SHELDON, RA
RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY, 1995, 114 (4-5): : 171 - 174
[34] AMINO-ACID NORFLOXACIN DERIVATIVES AS PRODRUGS
HRIBARKIKELJ, A
FERCEJTEMELJOTOV, D
ZMITEK, J
PHARMAZIE, 1993, 48 (01): : 64 - 65
[35] Construction of 3-amino-2-oxindoles by direct amination of aniline or α-amino-acid derivatives to 3-bromooxindoles
Zhao, Min
Li, Nai-Kai
Zhang, Ya-Fei
Pan, Feng-Feng
Wang, Xing-Wang
TETRAHEDRON, 2016, 72 (10) : 1406 - 1414
[36] HYPOGLYCEMIC COMPOUNDS - AMINO-ACID DERIVATIVES OF SULFONYLUREA .2.
VICENTINI, CB
GUARNERI, M
SARTO, G
FARMACO-EDIZIONE SCIENTIFICA, 1983, 38 (09): : 672 - 678
[37] Difluorocarbene-induced [1,2]- and [2,3]-Stevens rearrangement of tertiary amines
Su, Jianke
Guo, Yu
Li, Chengbo
Song, Qiuling
NATURE COMMUNICATIONS, 2024, 15 (01)
[38] [2,3]-Sigmatropic Rearrangement of Ynamides: Preparation of α-Amino Allenephosphonates
Gomes, Filipe
Fadel, Antoine
Rabasso, Nicolas
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (12): : 5439 - 5444
[39] An Ireland-Claisen rearrangement approach to β2,3-amino acids
Ylioja, Paul M.
Mosley, Alexander D.
Charlot, Claire E.
Carbery, David R.
TETRAHEDRON LETTERS, 2008, 49 (07) : 1111 - 1114
[40] Synthesis of Functionalized β-Keto Arylthioethers by the Aryne Induced [2,3] Stevens Rearrangement of Allylthioethers
Thangaraj, Manikandan
Gaykar, Rahul N.
Roy, Tony
Biju, Akkattu T.
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (08): : 4470 - 4476

← 1 2 3 4 5 →