24530-01-6

Upstream product

• 121-97-1 4-Methoxypropiophenone 
• 213598-45-9 3,4-isopropylidenedioxy-Δ¹-pyrroline-1-oxide 
• 4437-51-8 3,4-hexanedione 
• 925-90-6 ethylmagnesium bromide 
• 1226-42-2 1,2-bis(4-methoxyphenyl)-1,2-ethanedione 

Downstream Products

• 115-42-4 4,4-bis-(4-methoxy-phenyl)-hexan-3-one 
• 20615-56-9 3.4-Di-<4-oxo-cyclohexen-(1)-yl>-hexandiol-(3.4) 
• 96364-84-0 3,4-Di-<4-methoxy-cyclohexadien-(1,4)-yl>-hexan-diol-(3,4) 

Relevant academic research and scientific papers

A flexible enantioselective approach to 3,4-dihydroxyprolinol derivatives by SmI2-mediated reductive coupling of chiral nitrone with ketones/aldehydes

A flexible enantioselective approach to polyhydroxylated prolinol derivatives was described, which is based on the samarium diiodide-mediated reductive coupling of the chiral nitrone (3S,4R)-8, derived from d-isoascorbic acid with aldehydes/ketones. Thereby, polyhydroxyprolinol derivatives 9a-e and 9h-j were obtained from aromatic ketones and aliphatic aldehydes in good to excellent yields of 65-91%. These reductive hydroxyalkylations are highly diastereoselective in establishing the C-4 stereogenic center. By this way, the asymmetric syntheses of (-)-8a-epi-swainsonine (4) and (-)-8,8a-di-epi- swainsonine (5) have been achieved.

Stereochemistry and Side Products in Reductive Coupling of Alkyl Aryl Ketones to 1,2-Dialkyl-1,2-diarylethylenes

The reductive coupling of alkyl aryl ketones 1 - 3 and 7 - 9 by low valent titanium salts yields predominantly the (Z)-isomers of 11 - 13 and 17 - 19.Evidence is given by 1H NMR spectroscopy.This behavior can be explained by ?-complex formation of phenyl rings with Ti0.Severe steric hindrance, however, favors the (E)-isomers ( -> 14 and 15).Donor groups in p-position, particularly, give increasing amounts of pinacols, 23 - 27, which undergo rearrangement to the ketones 28 and 29.