One-pot synthesis of 3-functionalized (Z)-silyl enol ethers from 1-arylallylic alcohols by C,O-difunctionalization of dipotassio α,β-dianion intermediates

被引：1

作者：

Hayashi, Rikuo ^{[1
]}

Narita, Yutaka ^{[1
]}

Sai, Masahiro ^{[1
]}

机构：

[1] Gifu Univ, Fac Engn, Dept Chem & Biomol Sci, 1-1 Yanagido, Gifu 5011193, Japan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2023年 / 21卷 / 20期

关键词：

ALPHA-SILOXYALLYLSILANES; ORGANOSILICON COMPOUNDS; ALLYLOXY CARBANIONS; BROOK REARRANGEMENT; SILYL ETHERS; CARBONYL; ALKYLATION; ARYLATION; KETONES; FUNCTIONALIZATION;

D O I：

10.1039/d3ob00199g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Previously reported syntheses of 3-functionalized silyl enol ethers using allyloxysilanes are hindered by undesirable reactions owing to retro Brook rearrangements. In this study, various 3-functionalized (Z)-silyl enol ethers were synthesized from readily available 1-arylallylic alcohols using (trimethylsilyl)methylpotassium as a base. C,O-Difunctionalization of the in situ-generated dipotassio alpha,beta-dianion with electrophiles and silyl chlorides is key to the success of this transformation. Control experiments confirmed that the dianion has higher nucleophilicity and thermal stability than related siloxyallylpotassiums.

引用

页码：4206 / 4209

页数：4

共 17 条

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ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (06) : 826 - 833
[2] One-Pot Synthesis of Silylated Enol Triflates from Silyl Enol Ethers for Cyclohexynes and 1,2-Cyclohexadienes
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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (25) : 3343 - 3347
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TETRAHEDRON, 2007, 63 (23) : 4929 - 4936
[4] One-pot synthesis of functionalized carbacycles by formal [3+3] cyclizations of 1,3-bis(silyl enol ethers) with 1,3-dielectrophiles
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Langer, Peter
SYNTHESIS-STUTTGART, 2007, (03): : 327 - 347
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Mamat, Constantin
Pundt, Thomas
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Reinke, Helmut
Koeckerling, Martin
Langer, Peter
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (03) : 492 - 502
[6] Heck reactions starting from silyl enol ethers - A simple one-pot nonaflation-coupling procedure for the synthesis of 1,3-dienes
Webel, M
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SYNLETT, 1997, (10) : 1141 - &
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Pundt, Thomas
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Hussain, Ibrar
Yawer, Mirza A.
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Langer, Peter
TETRAHEDRON LETTERS, 2007, 48 (15) : 2745 - 2747
[8] One-pot synthesis of 6-(pyridyl)salicylates by formal [3+3] cyclizations of 1,3-bis(silyl enol ethers) with 3-pyridyl-3-silyloxy-2-en-1-ones
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SYNTHESIS-STUTTGART, 2008, (08): : 1276 - 1282
[9] ONE-POT SYNTHESIS OF HOMOALLYLIC ALCOHOLS FROM 1,3-DIENES - TANDEM VICINAL DIFUNCTIONALIZATION OF 1,3-DIENES BY HYDRIDE ADDITION-ALDEHYDE COUPLING SEQUENCE VIA ORGANOSILICON INTERMEDIATES
KOBAYASHI, S
NISHIO, K
SYNTHESIS-STUTTGART, 1994, (05): : 457 - 459
[10] Diversity-oriented synthesis of functionalized 1-aminopyrroles by regioselective zinc chloride-catalyzed, one-pot 'Conjugate Addition/Cyclization' reactions of 1,3-bis(silyl enol ethers) with 1,2-diaza-1,3-butadienes
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Mkrtchyan, Satenik
Schmidt, Andreas
Attanasi, Orazio A.
Favi, Gianfranco
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ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (09) : 1331 - 1336

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