Stereoselective access to the versatile 4-aminohex-5-ene-1,2,3-triol pattern

被引：12

作者：

Ayad, T ^{[1
]}

Faugeroux, V ^{[1
]}

Génisson, Y ^{[1
]}

André, C ^{[1
]}

Baltas, M ^{[1
]}

Gorrichon, L ^{[1
]}

机构：

[1] Univ Toulouse 3, CNRS, UMR 5068, Lab Synth & Physicochim Mol Interet Biol, F-31062 Toulouse 04, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 25期

关键词：

D O I：

10.1021/jo048766v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We developed a stereocontrolled route allowing potential access to the eight isomers of 4-benzylaminohex-5-ene-1,2,3-triol in two or four steps and ca. 50% yield from readily available chiral nonracemic cis- or trans-alpha,beta-epoxyimine precursors. A new (NH4)(2)CO3-based carboxylation/intramolecular cyclization sequence allowed regio- and stereocontrolled C-3 epoxide opening while neat C-2 hydrolysis was ensured by simple aqueous acidic treatment.

引用

页码：8775 / 8779

页数：5

共 16 条

[1] Concise asymmetric syntheses of (-)-lentiginosine and of its pyrrolizidinic analogue
Ayad, T
Génisson, Y
Baltas, M
Gorrichon, L
[J]. CHEMICAL COMMUNICATIONS, 2003, (05) : 582 - 583
[2] A flexible route towards five-membered ring imino sugars and their novel 2-deoxy-2-fluoro analogues
Ayad, T
Génisson, Y
Broussy, S
Baltas, M
Gorrichon, L
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (15) : 2903 - 2910
[3] Ayad T, 2001, SYNLETT, P866
[4] ASYMMETRIC-SYNTHESIS VIA NUCLEOPHILIC-ADDITION TO ALPHA,BETA-EPOXYIMINES
BERESFORD, KJM
HOWE, GP
PROCTER, G
[J]. TETRAHEDRON LETTERS, 1992, 33 (23) : 3355 - 3358
[5] A critical outlook and comparison of enantioselective oxidation methodologies of olefins
Bonini, C
Righi, G
[J]. TETRAHEDRON, 2002, 58 (25) : 4981 - 5021
[6] EFFECT OF CARBONYL + RELATED GROUPS ON REACTIVITY OF HALIDES IN SN2 REACTIONS
BORDWELL, FG
BRANNEN, WT
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (21) : 4645 - &
[7] DIASTEREOFACE DIFFERENTIATION IN ADDITION OF LITHIUM ENOLATES TO CHIRAL ALPHA,BETA-EPOXYALDEHYDES
ESCUDIER, JM
BALTAS, M
GORRICHON, L
[J]. TETRAHEDRON, 1993, 49 (24) : 5253 - 5266
[8] A MILD OXIDIZING REAGENT FOR ALCOHOLS AND 1,2-DIOLS - O-IODOXYBENZOIC ACID (IBX) IN DMSO
FRIGERIO, M
SANTAGOSTINO, M
[J]. TETRAHEDRON LETTERS, 1994, 35 (43) : 8019 - 8022
[9] An aldol-based approach to the synthesis of the antibiotic Anisomycin
Hulme, AN
Rosser, EM
[J]. ORGANIC LETTERS, 2002, 4 (02) : 265 - 267
[10] SYNTHESIS OF 5-MEMBERED HETEROCYCLES BY REACTIONS OF N-SUBSTITUTED-2-AMINOMETHYLOXIRANES WITH HETEROCUMULENES
KARIKOMI, M
YAMAZAKI, T
TODA, T
[J]. CHEMISTRY LETTERS, 1993, (11) : 1965 - 1968

← 1 2 →