Julia-Kocienski Olefination: A Tutorial Review

被引：14

作者：

Sakaine, Guna ^{[1
]}

Leitis, Zigmars ^{[1
]}

Locmele, Rebeka ^{[1
]}

Smits, Gints ^{[1
]}

机构：

[1] Latvian Inst Organ Synth, Lab CNS Act Cpds, Aizkraukles 21, Riga, Latvia

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 26卷 / 07期

关键词：

Julia-Kocienski olefination; natural products; total synthesis; synthetic methods; stereoselectivity; ENANTIOSELECTIVE TOTAL-SYNTHESIS; CARBONYL-COMPOUNDS; SULFONES; DERIVATIVES; STEREOCHEMISTRY; ASSIGNMENT;

D O I：

10.1002/ejoc.202201217

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Over the past two decades, Julia-Kocienski olefination has become one of the most powerful and reliable C=C double-bond construction methods typically furnishing E-configured alkenes. This review summarizes the scientific literature of the past decade focusing on the key aspects for successful execution of the olefination step. The main stereoselectivity and yield-determining aspects have been outlined in separate chapters providing all the necessary information for the synthesis of Julia-Kocienski reagents as well as the most commonly used reaction optimization techniques.

引用

页数：9

共 50 条

[21] Sultones and Sultines via a Julia-Kocienski Reaction of Epoxides
Smith, Geoffrey M. T.
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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (50) : 15236 - 15240
[22] Synthesis of C-glycoside analogs via a one-pot Julia-Kocienski olefination reaction.
Chen, GW
Franck, RW
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U206 - U207
[23] Julia-Kocienski approach to trifluoromethyl-substituted alkenes
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Mandal, Samir K.
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TETRAHEDRON LETTERS, 2013, 54 (45) : 6008 - 6011
[24] Convergent synthesis of functionalized fluoroallylamines by the Julia-Kocienski reaction
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Pfund, Emmanuel
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TETRAHEDRON, 2011, 67 (07) : 1398 - 1405
[25] Synthesis of tetrahedral diarylheptanoid ent-diospongin A and epimer-diospongin B by employing Julia-Kocienski olefination
Meruva, Suresh Babu
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Raghunadh, Akula
Rao, K. Raghavendra
Dahanukar, Vilas H.
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TETRAHEDRON LETTERS, 2014, 55 (34) : 4739 - 4741
[26] Palladium-Catalyzed S-Allylation of Vinyl Carbinols - Total Syntheses of Carotenoids by Julia-Kocienski Olefination
Golikov, Aleksei N.
Seo, Chibeom
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Koo, Sangho
ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (01) : 82 - 90
[27] Mechanistic Manifold and New Developments of the Julia-Kocienski Reaction
Aissa, Christophe
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (12) : 1831 - 1844
[28] Simple protocol for enhanced (E)-selectivity in Julia-Kocienski reaction
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TETRAHEDRON LETTERS, 2011, 52 (18) : 2348 - 2352
[29] Computational study of the Julia-Kocienski methylenation of acetone using DFT
Korman, Matthew
Beck, Jordan
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
[30] 3,5-bis(trifluoromethyl)phenyl sulfones in the Julia-Kocienski olefination - Application to the synthesis of tri- and tetrasubstituted olefins
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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (20) : 4747 - 4754

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