New route to 4-aminocyclopent-2-en-1-ols: Synthesis and enantioselective rearrangement of 4-amino-substituted cyclopentene oxides

被引：40

作者：

Barrett, S ^{[1
]}

O'Brien, P ^{[1
]}

Steffens, HC ^{[1
]}

Towers, TD ^{[1
]}

Voith, M ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

来源：

TETRAHEDRON | 2000年 / 56卷 / 49期

关键词：

amino alcohols; epoxidation; stereocontrol; nucleosides;

D O I：

10.1016/S0040-4020(00)00911-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new route for the asymmetric synthesis of 4-aminocyclopent-2-en-1-ols (90% ee) for carbocyclic nucleoside analogue synthesis is described. The approach involves the stereoselective preparation of cis 4-amino-substituted cyclopentene oxides and subsequent chiral base-mediated rearrangement to the corresponding allylic alcohols. Full details on the synthesis and stereoselectivity of epoxidation of 4-amino-substituted cyclopentenes are presented. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：9633 / 9640

页数：8

共 50 条

[21] NEW THIENO COMPOUNDS .12. SYNTHESIS OF 4-AMINO-SUBSTITUTED THIENO[2,3-D]PYRIMIDIN-2-YLACETIC ACID-DERIVATIVES
PECH, R
EISENACHER, T
BOHM, R
PHARMAZIE, 1992, 47 (01): : 20 - 21
[22] Synthesis of anti-2-aryl-4-en-1-ols from the corresponding syn isomers
V. I. Boev
A. I. Moskalenko
S. L. Belopukhov
Russian Journal of Organic Chemistry, 2017, 53 : 624 - 625
[23] Synthesis of anti-2-aryl-4-en-1-ols from the corresponding syn isomers
Boev, V. I.
Moskalenko, A. I.
Belopukhov, S. L.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 53 (04) : 624 - 625
[24] KOtBu-promoted three-component coupling of aldehydes and alkynes:: Highly efficient synthesis of 1-En-4-yn-3-ols and 2-En-4-yn-1-ols
Wang, Shao-Hua
Tu, Yong-Qiang
Chen, Peng
Hu, Xiang-Dong
Zhang, Fu-Min
Wang, Ai-Xia
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (11): : 4343 - 4345
[25] Facile synthesis of cis-4-amino-2-cyclopentene-1-methanol, a key intermediate for the synthesis of carbocyclic nucleosides
An, GI
Rhee, H
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2002, 21 (01): : 65 - 72
[26] NEW THIENO COMPOUNDS .14. SYNTHESIS OF 4-AMINO-SUBSTITUTED THIENO[2,3-D]PYRIMIDINE-6-CARBOXYLIC ACID-DERIVATIVES
BAUMGARTNER, A
PECH, R
BOHM, R
PHARMAZIE, 1993, 48 (03): : 192 - 194
[27] A NEW SYNTHESIS OF 2-AMINO-1-THIACHROMONES-4
VOLOVENKO, YM
LITENKO, VA
DASHKOVSKAYA, YV
BABICHEV, FS
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1982, (08): : 1047 - 1048
[28] A NEW ROUTE TO THE SYNTHESIS OF 2-AMINO-6-(METHOXYCARBONYL)AMINO-4-(TETRAHYDROPYRIDYL)PYRIMIDINE 1-OXIDE
MULLER, JC
RAMUZ, H
WAGNER, HP
HELVETICA CHIMICA ACTA, 1983, 66 (03) : 809 - 813
[29] Synthesis of new substituted 1λ4-1,2,4,6-thiatriazines
Stoller, AD
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2000, 37 (03) : 583 - 595
[30] Gold-catalyzed cyclization of (Z)-2-en-4-yn-1-ols:: Highly efficient synthesis of fully substituted dihydrofurans and furans
Liu, YH
Song, FJ
Song, ZQ
Liu, MN
Yan, B
ORGANIC LETTERS, 2005, 7 (24) : 5409 - 5412

← 1 2 3 4 5 →