Synthesis and Application of a New Bisphosphite Ligand Collection for Asymmetric Hydroformylation of Allyl Cyanide was written by Cobley, Christopher J.;Gardner, Kelli;Klosin, Jerzy;Praquin, Celine;Hill, Catherine;Whiteker, Gregory T.;Zanotti-Gerosa, Antonio;Petersen, Jeffrey L.;Abboud, Khalil A.. And the article was included in Journal of Organic Chemistry in 2004.Synthetic Route of C24H34O2 This article mentions the following:
A series of mono- and bidentate phosphites was prepared with (S)-5,5′,6,6′-tetramethyl-3,3′-di-tert-butyl-1,1′-biphenyl-2,2′-dioxy [(S)-BIPHEN] as a chiral auxiliary and screened in the asym. hydroformylation of butenenitrile. These hydroformylation results were compared with those of two existing chiral ligands, Chiraphite and BINAPHOS, whose utility in asym. hydroformylation has been previously demonstrated. One bis(phosphite) with a 2,2′-biphenol bridge was found to be the best overall ligand for asym. hydroformylation of allyl cyanide with up to 80% ee and regioselectivities (branch-to-linear ratio, b/l) of 20 with turnover frequency of 625 [h-1] at 35 °C. BINAPHOS gave enantioselectivities up to 77% ee when the reaction was conducted in either acetone or neat but with poor regioselectivity (b/l 2.8) and activities 7 times lower than that of (S,S)-Kelliphite [(S,S)-I]. The product of butenenitrile hydroformylation using (11aR,11’aR)-[[[1,1′-biphenyl]diyl]bis(oxy)]bis[dibenzo[d,f][1,3,2]dioxaphosphepin], i.e. (R,R)-I [(R,R)-Kelliphite] was subsequently transformed into (R)-4-amino-2-methyl-1-butanol, a useful chiral building block. Single-crystal X-ray structures of (S,S)-I and its rhodium complex were determined In the experiment, the researchers used many compounds, for example, (S)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol (cas: 205927-03-3Synthetic Route of C24H34O2).
(S)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol (cas: 205927-03-3) belongs to copper catalysts. The transition metal-catalyzed chemical transformation of organic electrophiles and organometallic reagents has turned up as an exceedingly robust synthetic tool. Copper nanoparticles can also catalyze the coupling reaction of nitrogen-containing nucleophiles, phenols, thiols, xanthogenates, selenium ruthenium nucleophiles and the like.Synthetic Route of C24H34O2
Referemce:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”