SYNTHESIS OF CHIRAL 4-ALKYL 4-HYDROXY CYCLOPENTENONES VIA A DIASTEREOSELECTIVE TANDEM AZA-COPE/MANNICH CYCLIZATION REACTION FROM ALDEHYDOSUGAR

被引：23

作者：

KUHN, C

LEGOUADEC, G

SKALTSOUNIS, AL

FLORENT, JC

机构：

[1] INST CURIE,CNRS,CHIM LAB,BIOL SECT,F-75231 PARIS 05,FRANCE

[2] UNIV ATHENS,DEPT PHARM,DIV PHARMACOGNOSY,GR-15771 ATHENS,GREECE

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 18期

关键词：

D O I：

10.1016/0040-4039(95)00473-P

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient construction of chiral 4-hydroxy 2-cyclopentenones from alpha-alkoxy aldehyde 6 derived from sugar is reported. A mechanism is proposed involving imine-enamine equilibrium, then alkylation with 2-alkoxypropenyl iodide followed by a tandem 3-aza-Cope/intramolecular Mannich reaction in a one-pot process.

引用

页码：3137 / 3140

页数：4

共 5 条

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McDaid, E
TETRAHEDRON LETTERS, 2002, 43 (05) : 903 - 905
[2] A NEW ACCESS TO KAINOIDS VIA A TANDEM AZA-COPE/MANNICH REACTION - APPLICATION TO THE ENANTIOSELECTIVE SYNTHESIS OF (-)-ALPHA-ALLOKAINIC ACID
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[3] Domino aza-Claisen/Mannich cyclization reaction from a chiral α-alkoxy enamine or sequential alkylation of an α-alkoxy ester enolate or nitrile anion, followed by an intramolecular Wittig reaction:: Two (3+2) annulation routes to homochiral 4-alkyl-4-hydroxy-2-cyclopentenone synthesis
Kuhn, C
Skaltsounis, L
Monneret, C
Florent, JC
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (14) : 2585 - 2595
[4] Formal [3+2] cycloaddition reaction of [1,4]oxazin-2-ones and α-alkynyl ketones via a tandem Mukaiyama-Aldol addition/aza-cope rearrangement
Obrecht, D
Zumbrunn, C
Müller, K
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (18): : 6891 - 6895
[5] Synthesis of Halogenated Cyclic Enamines from Cyclic N-2-En-4-ynyl-N-1-ynylamides and N-Propargyl-N-1-ynylamides via a Tandem Iron Halide Promoted N-to-C Shift-Aza-Prins Cyclization Sequence
Lin, Hsin-Hui
Chiang, Tai-Ching
Wu, Rong-Xuan
Chang, Yi-Mei
Wang, Hao-Wen
Liu, Ssu-Ting
Yeh, Ming-Chang P.
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (06) : 1277 - 1282

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