Regio- and stereoselective synthesis of tetrasubstituted allylic alcohols by three-component reaction of acetylenic sulfone, dialkylzinc, and aldehyde

Xie, Meihua; Lin, Gaofeng; Zhang, Jinhua; Li, Ming; Feng, Chengyou

doi:10.1016/j.jorganchem.2010.01.003

Cited by 13 publications

(3 citation statements)

References 25 publications

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“…Various organozinc reagents can be used, irrespective of the identity of the organic groups, preparative protocols, and accompanying functional groups (Table 1). Similarly, Xie reported ethyl- or methylzincation of alkynyl sulfones [42] and Tanaka reported carbozincation of alkynyl sulfoxides [43–44]. …”

Section: Reviewmentioning

confidence: 99%

Recent advances in transition-metal-catalyzed intermolecular carbomagnesiation and carbozincation

Murakami¹,

Yorimitsu²

2013

Beilstein J. Org. Chem.

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SummaryCarbomagnesiation and carbozincation reactions are efficient and direct routes to prepare complex and stereodefined organomagnesium and organozinc reagents. However, carbon–carbon unsaturated bonds are generally unreactive toward organomagnesium and organozinc reagents. Thus, transition metals were employed to accomplish the carbometalation involving wide varieties of substrates and reagents. Recent advances of transition-metal-catalyzed carbomagnesiation and carbozincation reactions are reviewed in this article. The contents are separated into five sections: carbomagnesiation and carbozincation of (1) alkynes bearing an electron-withdrawing group; (2) alkynes bearing a directing group; (3) strained cyclopropenes; (4) unactivated alkynes or alkenes; and (5) substrates that have two carbon–carbon unsaturated bonds (allenes, dienes, enynes, or diynes).

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Section: Reviewmentioning

confidence: 99%

Recent advances in transition-metal-catalyzed intermolecular carbomagnesiation and carbozincation

Murakami¹,

Yorimitsu²

2013

Beilstein J. Org. Chem.

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“…Copper-catalyzed carbozincation could also be performed under very different conditions (toluene, reflux) and a single isomer was still obtained [53]. 1-Alkynyl sulfoximines behave similarly to alkynyl sulfones and the addition of an organocopper reagent usually leads to two isomers in variable amounts.…”

Section: Reviewmentioning

confidence: 99%

Recent advances in carbocupration of α-heterosubstituted alkynes

Basheer¹,

Marek²

2010

Beilstein J. Org. Chem.

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SummaryCarbocupration of α-heterosubstituted alkynes leads to the formation of stereodefined functionalized vinyl copper species as single isomer. Recent advances in the field show that a simple pre-association of the organometallic derivative with an additional polar functional group in the vicinity of the reaction center may completely change the stereochemical outcome of the reaction. Representative examples are given in this mini-review.

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“…Similar to phosphorus, sulfur forms diverse stable organic compounds in various oxidation states. The known examples of copper-catalyzed carbomagnesiation 8,9 and carbozincation 10,11 of alkynyl sulfones as well as carbozincation 12,13 of alkynyl sulfoxides gave hope that carboalumination of alkynyl sulfur derivatives would also proceed successfully.…”

mentioning

confidence: 99%

Zirconocene Catalysis in Organoaluminum Synthesis of 1-Alkenyl Sulfones and Sulfides

et al. 2016

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Regio- and stereoselective synthesis of tetrasubstituted allylic alcohols by three-component reaction of acetylenic sulfone, dialkylzinc, and aldehyde

Cited by 13 publications

References 25 publications

Recent advances in transition-metal-catalyzed intermolecular carbomagnesiation and carbozincation

Recent advances in transition-metal-catalyzed intermolecular carbomagnesiation and carbozincation

Recent advances in carbocupration of α-heterosubstituted alkynes

Zirconocene Catalysis in Organoaluminum Synthesis of 1-Alkenyl Sulfones and Sulfides

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