155907-01-0

Upstream product

• 137037-08-2 (1R,2S)-2-acetoxy-1-methyl-3-cyclohexenecarbaldehyde 
• 935693-40-6 C₂₇H₅₂Si₂O₇ 
• 935693-39-3 C₂₇H₅₀Si₂O₇ 
• 935693-38-2 C₂₇H₅₂Si₂O₈ 
• 935693-37-1 C₂₈H₅₄Si₂O₈ 
• 935693-33-7 C₂₆H₅₀Si₂O₈ 
• 935693-31-5 C₂₇H₅₂Si₂O₇ 
• 136962-61-3 (1R,2S)-2-<(N,N-dimethylcarbamoyl)oxy>-1-methyl-3-cyclohexenecarbaldehyde 

Downstream Products

• 106758-72-9 (1S,2S)-2-(hydroxymethyl)-2-methylcyclohexanol 

Relevant academic research and scientific papers

Stereoselective double alkylation of the acetoacetate ester α-carbon on a D-glucose-derived template: Application to the synthesis of enantiopure cycloalkenones bearing an asymmetric quaternary carbon

The previously developed D-glucose derivative, i.e., methyl 6-deoxy-2,3-di-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside, served as a significant stereocontrolling element for the diastereoselective alkylation of the α-carbon in its acetoacetate at C-4

Asymmetric catalysis of Diels-Alder cycloadditions by an MS-free binaphthol-titanium complex: Dramatic effect of MS, linear vs positive nonlinear relationship, and synthetic applications

Asymmetric Diets-Aider (D.-A.) reaction of 5-hydroxynaphthoquinone (juglone) with butadienyl acetate catalyzed by the binaphthol-derived chiral titanium (BINOL-Ti) complex 1 proceeds in only 9% ee in the presence of molecular sieves (MS). Remarkably, however, this reaction proceeds in 76-96% ee with BINOL-Ti complex 1 freed from MS to provide the endo-adducts useful for the synthesis of anthracyclines and tetracyclines. The solid MS-free BINOL-Ti complex 1 is stable for months at -20°C. Enhancements in endo selectivity and asymmetric induction are observed with the MS-free BINOL-Ti 1 also in the catalyzed D.-A. cycloaddition of methacrolein and glyoxylate with 1,3-dienol ethers and esters. The glyoxylate adducts can be converted to the mevinolin (compactin) intermediates. Surprisingly, the MS-free complex 1 exhibits not only a linear relationship between the ee's of BINOL-Ti 1 and the D.-A. products but also a positive nonlinear effect (asymmetric amplification), depending simply on the mixing manner of (R)-1 with (S)-1 or (±)-1.

Chiral titanium complex-catalyzed Diels-Alder reaction: A practical route to anthracycline intermediates

Asymmetric Diels-Alder reactions of methacrolein and 1,4-naphthoquinone with 1,3-dienol derivatives catalyzed by the chiral binaphthol (BINOL)-derived titanium complex 1 are shown to provide the corresponding endo-adducts in high enantiomeric purity. The