446879-29-4

Upstream product

• 37778-99-7 (S)-2-phenyl-1-propanol 
• 122-78-1 phenylacetaldehyde 
• 1333203-99-8 C₁₅H₁₄OS₂ 
• 286967-31-5 2(S)-phenyl-1-propanol methanesulfonate 

Downstream Products

• 2406-18-0 methyl (R)-(-)-4-phenylpentanoate 
• 1612882-49-1 C₁₄H₁₈O₄ 
• 446879-35-2 (5R)-phenyliodonium 1-[(nonafluorobutyl)sulfonyl]-2-oxo-5-phenylhexylide 
• 446879-32-9 (R)-phenyliodonium 1-methoxy-1,3-dioxo-6-phenylheptylide 
• 446879-31-8 (R)-methyl 2-diazo-3-oxo-6-phenylheptanoate 
• 446879-33-0 (R)-2-Methyl-5-oxo-2-phenyl-cyclopentanecarboxylic acid methyl ester 
• 53750-06-4 (R)-methyl 3-oxo-1-phenylcyclopentanecarboxylate 
• 446879-34-1 (R)-1-[(nonafluorobutyl)sulfonyl]-5-phenylhexan-2-one 
• 446879-30-7 (R)-methyl 3-oxo-6-phenylheptanoate 

Relevant academic research and scientific papers

A straightforward organocatalytic alkylation of 2-arylacetaldehydes: An approach towards bisabolanes

A highly stereoselective organocatalytic aalkylation of 2-arylacetaldehydes with a commercially available carbenium tetrafluoroborate is described. The stereoselective alkylation was carried out in acetonitrile/ water, under air in the presence of a commercially available imidazolidinone (MacMillan's catalyst). Key intermediates for the synthesis of bisabolanes were obtained through a simple chemistry. In particular a direct, enantioselective and facile synthesis of (R)-(-)-curcumene is described.

The enantioselectivity and the stereochemical course of copper-catalyzed intramolecular CH insertions of phenyliodonium ylides

The Cu-catalyzed intramolecular CH insertion of phenyliodonium ylide 1b was investigated at 0° in the presence of several chiral ligands. Enantioselectivities varied in the range 38-72%, and were higher than those resulting from reaction of the diazo compound 1c at 65°. The intramolecular insertion of the enantiomerically pure methyl diazoacetate (R)-20 and of the corresponding phenyliodonium ylide (R)-21 proceeded to (R)-23 with retention of configuration with [Cu(hfa)2] (hfa = hexafluoroacetylacetone = 1,1,1,5,5,5-hexafluoropentane-2,4-dione) and [Rh2(OAc)4]. These results are consistent with a carbenoid mechanism for the Cu-catalyzed insertion with phenyliodonium ylides. However, the insertion of the perfluorosulfonated phenyliodonium ylide (R)-29 afforded with [Cu(hfa)2] as well as with [Rh2(OAc)4] the cyclopentanone derivative 30 as a cis/trans mixture with only 56-67% enantiomeric excess.

Non-chelation controlled 1,3-asymmetric induction in β-chiral acylsilanes

The diastereoselectivity of nucleophilic adition to β-chiral acylsilanes is examined, and our method is applied to the stereoselective synthesis of calcitriol lactone, a major metabolite of vitamin D3.