Publication

Selective syntheses with organometallics. Part XI. An efficient synthesis of a,b-unsaturated aldehydes by a four-carbon unit extension of Grignard reagents

Manfred Schlosser
1984
Journal Articles

Abstract

Oxirane I, prepd. by epoxidn. of (EtO)2CHCH2CH:CH2, reacted with Grignard reagents in the presence of catalytic CuBr to give 78-92% b-hydroxyacetals (EtO)2CHCH2CHR1OH [II; R1 = CH2CMe3, CH2CHMeEt, pentyl, CH2CH2CMe:CH2, CH2Ph, CH2CH2Ph, (CH2)7OR2; R2 = tetrahydropyranyl, SiMe3], which gave enals HCOCH:CHR1 in 50-85% yield on hydrolysis. Careful hydrolysis of II (R1 = CH2CMe3) gave HCOCH2CHR1OH, which formed H2C:CHCH2CHR1OH on Wittig reaction or dimerized to form 1,3-dioxane III. [on SciFinder (R)]

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https://infoscience.epfl.ch/entities/publication/f103e3c8-2f3f-4038-8ece-94661bd9d87f

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Manfred Schlosser
1984
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/f103e3c8-2f3f-4038-8ece-94661bd9d87f

About this result

Related concepts (21)

Grignard reagent

A Grignard reagent or Grignard compound is a chemical compound with the general formula , where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride and phenylmagnesium bromide . They are a subclass of the organomagnesium compounds. Grignard compounds are popular reagents in organic synthesis for creating new carbon-carbon bonds. For example, when reacted with another halogenated compound in the presence of a suitable catalyst, they typically yield and the magnesium halide as a byproduct; and the latter is insoluble in the solvents normally used.

Organoaluminium chemistry

Organoaluminium chemistry is the study of compounds containing bonds between carbon and aluminium. It is one of the major themes within organometallic chemistry. Illustrative organoaluminium compounds are the dimer trimethylaluminium, the monomer triisobutylaluminium, and the titanium-aluminium compound called Tebbe's reagent. The behavior of organoaluminium compounds can be understood in terms of the polarity of the C−Al bond and the high Lewis acidity of the three-coordinated species.

Total synthesis

Total synthesis is the complete chemical synthesis of a complex molecule, often a natural product, from simple, commercially-available precursors. It usually refers to a process not involving the aid of biological processes, which distinguishes it from semisynthesis. Syntheses may sometimes conclude at a precursor with further known synthetic pathways to a target molecule, in which case it is known as a formal synthesis. Total synthesis target molecules can be natural products, medicinally-important active ingredients, known intermediates, or molecules of theoretical interest.

Related publications (4)

Selective syntheses with organometallics. Part XI. An efficient synthesis of a,b-unsaturated aldehydes by a four-carbon unit extension of Grignard reagents

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On Reductions for Synthesis Procedures

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