Mannich Reactions of Carbohydrate Derivatives with Ketones To Afford Polyoxy-Functionalized Piperidines

被引：12

作者：

Maram, Lingaiah ^{[1
]}

Tanaka, Fujie ^{[1
]}

机构：

[1] Grad Univ, Okinawa Inst Sci & Technol, Chem & Chem Bioengn Unit, 1919-1 Tancha, Onna, Okinawa 9040495, Japan

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 04期

关键词：

DIELS-ALDER REACTIONS; ONE-POT SYNTHESIS; ASYMMETRIC-SYNTHESIS; MICHAEL ADDITION; ALDOL REACTIONS; ACCESS; ENONES; INHIBITORS; ISATINS; ARYL;

D O I：

10.1021/acs.orglett.9b00105

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mannich reactions of carbohydrate derivatives with ketones that afford polyoxy-functionalized piperidines are reported. Ketone nucleophiles (enamines/enolates) were generated in the presence of the amines used for the formation of the iminium ions of sugar derivatives with or without an additive. Conditions to preferentially generate piperidine derivatives rather than tetrahydrofurans were identified. Products from the reactions of allyl ketones were readily transformed to bicyclic piperidines.

引用

页码：1165 / 1169

页数：5

共 10 条

[1] Switching Electrophile Intermediates to Nucleophiles: Michael and Oxa-Diels-Alder Reactions to Afford Polyoxy-Functionalized Piperidine Derivatives with Tetrasubstituted Carbon
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ORGANIC LETTERS, 2020, 22 (07) : 2751 - 2755
[2] Organocatalytic enantioselective Mannich and retro-Mannich reactions and combinations of these reactions to afford tetrasubstituted α-amino acid derivatives
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[4] Synthesis of functionalized spirocyclic oxetanes through Paterno-Buchi reactions of cyclic ketones and maleic acid derivatives
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[5] anti-selective SMP-catalyzed direct asymmetric Mannich-type reactions:: synthesis of functionalized amino acid derivatives
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[6] AN INVESTIGATION OF DIELS-ALDER REACTIONS USING HIGHLY FUNCTIONALIZED ALPHA,BETA-UNSATURATED KETONES - AN APPROACH TO HYDRINDANE DERIVATIVES
SCHUDA, PF
EBNER, CL
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1984, 188 (AUG): : 11 - ORGN
[7] MANNICH REACTIONS IN A SERIES OF 6-MEMBERED HETEROCYCLIC GAMMA KETONES .5. AMINOETHYL DERIVATIVES OF TETRAHYDRO-1-THIOPYRAN-4-1 AND STEREOCHEMISTRY OF THEIR REDUCTION
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[8] Synthesis of functionalized 1-substituted alkenylsilanols and establishment of conditions for their palladium-catalyzed cross-coupling reactions to afford 1-substituted styrene derivatives
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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (20) : 4141 - 4147
[9] ACID-CATALYZED INTRAMOLECULAR C-ALKYLATION IN BETA,GAMMA-UNSATURATED DIAZOMETHYL KETONES .5. SYNTHESIS OF FUNCTIONALIZED HYDROFLUORENE DERIVATIVES VIA NOVEL FRAGMENTATION REACTIONS
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[10] ACID-CATALYZED INTRAMOLECULAR C-ALKYLATION IN BETA,GAMMA-UNSATURATED DIAZOMETHYL KETONES .4. SYNTHESIS OF FUNCTIONALIZED HYDROPHENANTHRENE AND BENZOCYCLODECENONE DERIVATIVES VIA NOVEL FRAGMENTATION REACTIONS, AND X-RAY STRUCTURAL-ANALYSES OF 2 ANGULARLY SUBSTITUTED HYDROPHENANTHRENE DERIVATIVESR
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