33603-30-4

Upstream product

• 1567-13-1 methyl cis-2-methyl-2-pentenoate 
• 818-58-6 methyl (E)-pent-3-enoate 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 504-60-9 penta-1,3-diene 
• 124-38-9 carbon dioxide 
• 15790-87-1 Methyl (E)-2-pentenoate 

Downstream Products

• 1364680-56-7 (S)-4-benzyl-3-((1E,3Z)-1-((tert-butyldimethylsilyl)oxy)-2-methylpenta-1,3-dien-1-yl)oxazolidin-2-one 
• 1364680-62-5 (S)-4-benzyl-3-((4R,5R,E)-5-hydroxy-2,4,7-trimethyloct-2-enoyl)oxazolidin-2-one 
• 1364681-46-8 (S)-(4R,5R,E)-8-((S)-4-benzyl-2-oxooxazolidin-3-yl)-2,5,7-trimethyl-8-oxooct-6-en-4-yl 3,3,3-trifluoro-2-methoxy-2-phenylpropanoate 
• 1364681-53-7 (R)-(4R,5R,E)-8-((S)-4-benzyl-2-oxooxazolidin-3-yl)-2,5,7-trimethyl-8-oxooct-6-en-4-yl 3,3,3-trifluoro-2-methoxy-2-phenylpropanoate 
• 1364680-75-0 (S)-4-benzyl-3-((4R,5R,E)-5-hydroxy-2,4-dimethylhex-2-enoyl)oxazolidin-2-one 
• 1364681-12-8 (S)-4-benzyl-3-((4R,5R,E)-5-cyclohexyl-5-hydroxy-2,4-dimethylpent-2-enoyl)oxazolidin-2-one 
• 1364681-19-5 (S)-4-benzyl-3-((4R,5R,E)-5-hydroxy-2,4-dimethyldec-2-enoyl)oxazolidin-2-one 
• 1364681-29-7 (S)-4-benzyl-3-((2E,4R,5R,6E)-5-hydroxy-2,4-dimethylocta-2,6-dienoyl)oxazolidin-2-one 
• 1364681-37-7 C₂₃H₂₅NO₄ 
• 1364681-07-1 (S)-4-benzyl-3-((4R,5R,E)-5-hydroxy-5-(2-methoxyphenyl)-2,4-dimethylpent-2-enoyl)oxazolidin-2-one 
• 1364681-60-6 (S)-(1R,2R,E)-5-((S)-4-benzyl-2-oxooxazolidin-3-yl)-1-(2-methoxyphenyl)-2,4-dimethyl-5-oxopent-3-en-1-yl 3,3,3-trifluoro-2-methoxy-2-phenylpropanoate 
• 1364681-67-3 (R)-(1R,2R,E)-5-((S)-4-benzyl-2-oxooxazolidin-3-yl)-1-(2-methoxyphenyl)-2,4-dimethyl-5-oxopent-3-en-1-yl 3,3,3-trifluoro-2-methoxy-2-phenylpropanoate 
• 1364680-50-1 (4S)-4-benzyl-3-((Z)-2-methylpent-3-enoyl)oxazolidin-2-one 

Relevant academic research and scientific papers

Syn -selective vinylogous Kobayashi aldol reaction

The Kobayashi aldol reaction has become a prominent transformation in polyketide syntheses. This methodology takes advantage of the directing effects of the Evans auxiliary and allows the stereoselective incorporation of a four carbon segment with two additional methyl branches establishing an anti-relationship between the two newly formed chiral centers. So far this transformation was restricted to anti-aldol products. We present here a modified protocol that provides the corresponding aldol product with high syn-selectivity.

Temperature-Dependent Alkylation of γ-Phenyl β,γ-Unsaturated Acid and Ester Systems in Hexamethylphosphortriamide-Tetrahydrofuran Solutions Using Lithium Diisopropylamide

The reactivities of some β,γ-unsaturated carboxylic acids and their methyl esters toward alkylation with methyl iodide using the lithium diisopropylamide-hexamethylphosphortriamide (LDA-HMPT) systems in THF have been investigated.The methylation selectivity of pent-3-enoic acid (2) and (1,2-dihydro-3-naphtyl)acetic acid (6) on using 1.0 equiv. of methyl iodide is high, the α-mono- to α,α-dimethylation ratios at -78 deg C being >20.The selectivity is substantially lower for styrylacetic acid (4) and increases with increasing temperature from 2.3 at -78 deg C to 8.5 at -10 deg C.The occurrence of dimethylation is ascribed to intermolecular proton exchange between the monomethylated species IIa and the nonmethylated species Ia.For the β,γ-unsaturated esters the methylation selectivity is somewhat higher than that for the corresponding carboxylic acids.

DIENCARBONSAEUREN AUS 1,3-DIENEN UND CO2 DURCH C-C-VERKNUEPFUNG AN NICKEL(0)

(Lig)Ni0 systems react with 1,3-dienes in the presence of CO2 to give nickela carboxylates.The influence of ligands and temperature on the regioselectivity of the C-C bond formation is elucidated.In some cases the nickela carboxylates undergo reductive elimination under the influence of maleic anhydride, and the coupled diene/CO2 moiety rearranges to give the diene carboxylic acid.A possible reaction sequence is discussed.