72681-07-3

Upstream product

• 75-16-1 methylmagnesium bromide 
• 36805-43-3 ethyl 3-methyl-5-phenylpent-2-enoate 
• 36805-43-3 ethyl (E)-3-methyl-5-phenylpent-2-enoate 
• 2550-26-7 4-Phenyl-2-butanone 
• 917-64-6 methyl magnesium iodide 
• 93893-89-1 3-methyl-5-phenylpent-2-enenitrile 

Downstream Products

• 1189241-02-8 (S)-4-methyl-4,6-diphenylhexan-2-one 
• 1189241-03-9 (R)-4-methyl-4,6-diphenylhexan-2-one 
• 312539-65-4 rac-4-methyl-6-phenyl-2-hexanone 
• 1242421-05-1 4-methyl-6-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexan-2-one 

Relevant academic research and scientific papers

Cobalt-Catalyzed Asymmetric 1,4-Hydroboration of Enones with HBpin

Herein, a series of new 8-OIQ cobalt complexes were synthesized and used for cobalt-catalyzed chemo- and enantioselective 1,4-hydroboration of enones with HBpin to access chiral β,β-disubstituted ketones with good to excellent chemo- and enantioselectivties. This protocol is operationally simple and shows a broad substrate scope.

Highly Enantioselective Iridium-Catalyzed Hydrogenation of Conjugated Trisubstituted Enones

Asymmetric hydrogenation of conjugated enones is one of the most efficient and straightforward methods to prepare optically active ketones. In this study, chiral bidentate Ir-N,P complexes were utilized to access these scaffolds for ketones bearing the stereogenic center at both the α- and β-positions. Excellent enantiomeric excesses, of up to 99%, were obtained, accompanied with good to high isolated yields. Challenging dialkyl substituted substrates, which are difficult to hydrogenate with satisfactory chiral induction, were hydrogenated in a highly enantioselective fashion.

Copper(II)-Catalyzed Tandem Decarboxylative Michael/Aldol Reactions Leading to the Formation of Functionalized Cyclohexenones

This work describes the development of a new single-pot copper(II)-catalyzed decarboxylative Michael reaction between β-keto acids and enones, followed by in situ aldolization, which results in highly functionalized chiral and achiral cyclohexenones. The achiral version of this Robinson annulation features a hitherto unprecedented Michael reaction of β-keto acids with sterically hindered β,β′-substituted enones and provides access to all carbon quaternary stereocenter-containing cyclohexenones (11 examples, 43-83% yield). In addition, an asymmetric chiral bis(oxazoline) copper(II)-catalyzed single-pot Robinson annulation has been devised for preparing chiral cyclohexenones, including some products that contain vicinal stereocenters (5 examples, 65-85% yield, 84-94% ee). This latter protocol has been successfully applied to the enantioselective formation of the oxygenated 10-nor-steroid core from readily available starting materials.

Synthesis of α-oxygenated β,γ-unsaturated ketones by a catalytic rearrangement strategy

A straightforward two-step entry to α-oxgenated β,γ-unsaturated ketones from readily available α,β-unsaturated ketones is disclosed. It was found that bis(allylic) alcohols undergo a skeletal rearrangement in the presence of 1 mol% of cheap and non-corros

Rearrangement Reactions Leading to Optically Active α,α-Disubstituted Primary Allylamines

Synthetic routes to α,α-disubstituted allylamines have been examined. Racemic compounds were conveniently prepared by thermal Overman rearrangements of primary allylic alcohols with trisubstituted double bonds, but rearrangement of these substrates using

Asymmetric conjugate reduction of α,β-unsaturated ketones and esters with chiral rhodium(2,6-bisoxazolinylphenyl) catalysts

New asymmetric conjugate reduction of β,β-disubstituted α,β-unsaturated ketones and esters was accomplished with alkoxylhydrosilanes in the presence of chiral rhodium(2,6-bisoxazolinylphenyl) complexes in high yields and high enantioselectivity. (E)-4-Phenyl-3-penten-2- one and (E)-4-phenyl-4-isopropyl-3-penten-2-one were readily reduced at 60°C in 95% ee and 98 % ee, respectively, by 1 mol % of catalyst loading. (EtO) 2MeSiH proved to be the best hydrogen donor of choice. tert-Butyl (E)-β-methylcinnamate and β-isopropylcinnamate could also be reduced to the corresponding dihydrocinnamate derivatives up to 98% ee.