Efficient one-pot synthesis of 1-chlorovinyl p-tolyl sulfoxides from aldehydes and ketones by the Horner-Wadsworth-Emmons reaction

被引：4

作者：

Kimura, Tsutomu ^{[1
]}

Kobayashi, Gen ^{[1
]}

Ijima, Shiori ^{[1
]}

Saito, Sae ^{[1
]}

Imafuji, Aki ^{[1
]}

Satoh, Tsuyoshi ^{[1
]}

机构：

[1] Tokyo Univ Sci, Grad Sch Sci, Dept Chem, Tokyo, Japan

来源：

HETEROATOM CHEMISTRY | 2017年 / 28卷 / 05期

关键词：

1-chlorovinyl p-tolyl sulfoxide; Fritsch-Buttenberg-Wiechell rearrangement; Horner-Wadsworth-Emmons reaction; magnesium alkylidene carbenoid; one-pot synthesis; MAGNESIUM ALKYLIDENE CARBENOIDS; INCLUDING ASYMMETRIC-SYNTHESIS; ALPHA-PHOSPHORYL SULFOXIDES; NUCLEOPHILIC-SUBSTITUTION; WIECHELL REARRANGEMENT; CONSECUTIVE REACTION; ELECTROPHILIC NATURE; CONJUGATE ADDITION; LITHIUM ACETYLIDES; WITTIG SYNTHESIS;

D O I：

10.1002/hc.21395

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A variety of 2-monosubstituted and 2,2-disubstituted 1-chlorovinyl p-tolyl sulfoxides was synthesized through a one-pot procedure by the Horner-Wadsworth-Emmons reaction of carbonyl compounds with [chloro(diethoxyphosphoryl)(p-tolylsulfinyl)methyl]lithium, which was generated from diethyl chlorophosphate, chloromethyl p-tolyl sulfoxide, and lithium diisopropylamide in advance. The in situ-prepared sulfoxides were directly converted into alkynes via the sulfoxide/magnesium exchange reaction with i-PrMgCl and the subsequent Fritsch-Buttenberg-Wiechell rearrangement of the resulting magnesium alkylidene carbenoids.

引用

页数：6

共 43 条

[1] Synthesis of cicerfuran, an antifungal benzofuran, and some related analogues [J].

Aslam, SN ;

Stevenson, PC ;

Phythian, SJ ;

Veitch, NC ;

Hall, DR .

TETRAHEDRON, 2006, 62 (17) :4214-4226

[2] The electrophilic nature of carbenoids, nitrenoids, and oxenoids [J].

Boche, G ;

Lohrenz, JCW .

CHEMICAL REVIEWS, 2001, 101 (03) :697-756

[3]

Braun M, 1998, ANGEW CHEM INT EDIT, V37, P430, DOI 10.1002/(SICI)1521-3773(19980302)37:4<430::AID-ANIE430>3.0.CO

[4]

2-5

[5] Anatomy of Long-Lasting Love Affairs with Lithium Carbenoids: Past and Present Status and Future Prospects [J].

Capriati, Vito ;

Florio, Saverio .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (14) :4152-4162

[6]

Eymery F, 2000, SYNTHESIS-STUTTGART, P185

[7] Palladium-Catalyzed Trifluoroethylation of Terminal Alkynes with 1,1,1-Trifluoro-2-iodoethane [J].

Feng, Yi-Si ;

Xie, Chuan-Qi ;

Qiao, Wen-Long ;

Xu, Hua-Jian .

ORGANIC LETTERS, 2013, 15 (04) :936-939

[8] Conversion of carbonyl compounds to alkynes: general overview and recent developments [J].

Habrant, Damien ;

Rauhala, Vesa ;

Koskinen, Ari M. P. .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (06) :2007-2017

[9] The Fritsch-Buttenberg-Wiechell rearrangement: modern applications for an old reaction [J].

Jahnke, Eike ;

Tykwinski, Rik R. .

CHEMICAL COMMUNICATIONS, 2010, 46 (19) :3235-3249

[10]

Katae T., 2011, SYNTHESIS-STUTTGART, V2011, P1435

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