75478-68-1

Upstream product

• 123-73-9 trans-Crotonaldehyde 
• 5425-44-5 2-Phenyl-[1,3]dithiane 
• 123-73-9 crotonaldehyde 
• 53178-41-9 2-lithio-2-phenyl-1,3-dithiane 

Downstream Products

• 128062-35-1 (E)-1-(2-Phenyl-[1,3]dithian-2-yl)-but-2-en-1-one 
• 354557-62-3 2-(3-chlorophenyl)-3-methyl-6-phenylpyridine 
• 128062-46-4 (R)-1-((1S,2S)-1-Oxo-2-phenyl-1λ⁴-[1,3]dithian-2-yl)-3-phenyl-butan-1-one 
• 128062-46-4 (S)-1-((1S,2S)-1-Oxo-2-phenyl-1λ⁴-[1,3]dithian-2-yl)-3-phenyl-butan-1-one 
• 128062-46-4 (R)-1-((1R,2S)-1-Oxo-2-phenyl-1λ⁴-[1,3]dithian-2-yl)-3-phenyl-butan-1-one 
• 128062-46-4 (S)-1-((1R,2S)-1-Oxo-2-phenyl-1λ⁴-[1,3]dithian-2-yl)-3-phenyl-butan-1-one 
• 128062-45-3 (S)-3-Methyl-1-((1S,2S)-1-oxo-2-phenyl-1λ⁴-[1,3]dithian-2-yl)-heptan-1-one 
• 128062-45-3 (R)-3-Methyl-1-((1S,2S)-1-oxo-2-phenyl-1λ⁴-[1,3]dithian-2-yl)-heptan-1-one 
• 128062-45-3 (S)-3-Methyl-1-((1R,2S)-1-oxo-2-phenyl-1λ⁴-[1,3]dithian-2-yl)-heptan-1-one 
• 128062-45-3 (R)-3-Methyl-1-((1R,2S)-1-oxo-2-phenyl-1λ⁴-[1,3]dithian-2-yl)-heptan-1-one 
• 128062-38-4 (E)-1-((1S,2R)-1-Oxo-2-phenyl-1λ⁴-[1,3]dithian-2-yl)-but-2-en-1-one 
• 128062-38-4 (E)-1-((1R,2R)-1-Oxo-2-phenyl-1λ⁴-[1,3]dithian-2-yl)-but-2-en-1-one 

Relevant academic research and scientific papers

Three-component coupling sequence for the regiospecific synthesis of substituted pyridines

A de novo synthesis of substituted pyridines is described that proceeds through nucleophilic addition of a dithiane anion to an α,β- unsaturated carbonyl followed by metallacycle-mediated union of the resulting allylic alcohol with preformed trimethylsilane-imines (generated in situ by the low-temperature reaction of lithium hexamethyldisilazide with an aldehyde) and Ag(I)- or Hg(II)-mediated ring closure. The process is useful for the convergent assembly of di- through penta-substituted pyridines with complete regiochemical control.

Stereoselectivity in the Conjugate Addition of Lithium Organocuprate Reagents to α,β-Unsaturated 2-Acyl-2-alkyl-1,3-dithiane 1-Oxides

α,β-Unsaturated 2-acyl-2-alkyl-1,3-dithiane 1-oxides undergo diastereoselective conjugate addition by lithium organocuprate reagents.Diastereoisomeric ratios of up to ca. 10:1 have been observed in the product mixtures.

ADDITION CONJUGUEE DE DERIVES LITHIES DE DITHIANE-1,3 AUX ALDEHYDES αβ ETHYLENIQUES

In order to synthesize γ carbonyl aldehydes which are interesting precursors in organic synthesis, we examine the action of masked acylanions, the lithiated derivatives from 1,3-dithiane 1a and 2-phenyl-1,3-dithiane on selected unsaturated aldehydes: crotonaldehyde 2, cinnamaldehyde 3, 3-methyl butenal 4 and methacrolein 5.In THF 1a leads with the four aldehydes to allylic alcohols.However 1b gives products resulting from C=C and C=O additions.Using THF-HMPA, we show that C=C addition is generally enhanced.Furthermore, in all cases examined C=C and C=O addition take place under kinetic controll: the regioselectivity observed can be interpreted by repulsive interactions due to the substrate and the reagent structure as well as lithium-carbonyl compound interactions.

1,4-ADDITION OF LITHIATED DERIVATIVES FROM 1,3-DITHIANES TO Α-UNSATURATED ALDEHYDES: A WAY TO Δ-CARBONYL ALDEHYDES

1,4-Addition of the lithiated derivatives of the 1,3-dithiane and 2-phenyl-1,3-dithiane on α-unsaturated aldehydes is performed in THF-HMPA ; this reaction could be an interesting way to δ-carbonyl aldehydes.