70633-78-2

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 36850-80-3 [(1-methoxyvinyl)oxy]trimethylsilane 
• 104-55-2 3-phenyl-propenal 
• 67-56-1 methanol 
• 420089-28-7 (2E,4E)-5-Phenyl-penta-2,4-dienoic acid methyl ester 
• 77086-38-5 ketene t-butyldimethylsilyl methyl acetal 

Downstream Products

• 90695-53-7 (2S,3S,4E)-(-)-3-Hydroxy-2-methyl-5-phenyl-4-pentensaeure-methylester 
• 88644-04-6 (2R,3S,4E)-(-)-3-Hydroxy-2-methyl-5-phenyl-4-pentensaeure-methylester 
• 90695-51-5 (2R,3S,4E)-(-)-2-Methyl-5-phenyl-4-penten-1,3-diol 
• 90664-11-2 (2R,3S,4E)-(+)-3-Methoxy-2-methyl-5-phenyl-4-penten-1-ol 
• 90664-13-4 (3R,4R,5E)-(+)-4-Methoxy-3-methyl-6-phenyl-5-hexennitril 
• 90664-09-8 (1E,3S,4R)-(-)-4-Methyl-5--1-phenyl-1-penten-3-ol 
• 90695-52-6 (3R,4R,5E)-(+)-4-Methoxy-3-methyl-6-phenyl-5-hexensaeure-methylester 
• 90664-10-1 (1E,3S,4R)-(-)-3-Methoxy-4-methyl-5--1-phenyl-1-penten 
• 90695-50-4 (2E,3R,4S,5E)-methyl 4-methoxy-2-(methoxymethylene)-3-methyl-6-phenylhex-5-enoate 
• 73341-71-6 (2Z,3R,4S,5E)-(+)-4-Methoxy-2-(methoxymethylen)-3-methyl-6-phenyl-5-hexensaeure-methylester 
• 90664-12-3 (2R,3S,4E)-(-)-(3-Methoxy-2-methyl-5-phenyl-4-pentenyl)-p-toluolsulfonat 

Relevant academic research and scientific papers

An improved asymmetric Reformatsky reaction mediated by (-)-N,N-dimethylaminoisoborneol

(-)-N,N-Dimethylaminoisoborneol ((-)-DAIB) was found to be an excellent ligand for the enantioselective addition of Reformatsky reagents to aromatic and aliphatic aldehydes. Enantioselectivities up to 93% ee were obtained with sulfur-containing aldehydes.

Configuration Sampling With Five-Membered Atropisomeric P,N-Ligands

Here we report a strategy for the systematic variation of atropisomeric C1-symmetric P,N ligands to incrementally change the position of the groups within the chiral pocket without modifying their steric parameters. More specifically, the effec

N-heterocyclic carbene-catalyzed radical reactions for highly enantioselective β-hydroxylation of enals

An N-heterocyclic carbene-catalyzed β-hydroxylation of enals is developed. The reaction goes through a pathway involving multiple radical intermediates, as supported by experimental observations. This oxidative single-electron-transfer reaction allows for highly enantioselective access to β-hydroxyl esters that are widely found in natural products and bioactive molecules.

Lewis base activation of Lewis acids: Catalytic, enantioselective addition of silyl ketene acetals to aldehydes

The concept of Lewis base activation of Lewis acids has been reduced to practice for catalysis of the aldol reaction of silyl ketene acetals and silyl dienol ethers with aldehydes. The weakly acidic species, silicon tetrachloride (SiCl4), can b

Lewis base activation of Lewis acids. Addition of silyl ketene acetals to aldehydes

The weak Lewis acid silicon tetrachloride can be activated by catalytic amounts of the chiral bisphosphoramide (R,R)-3 to form a highly reactive, chiral trichlorosilyl cation which is an extremely effective promoter of aldol addition reactions between ald

An in situ procedure for catalytic, enantioselective acetate aldol addition. Application to the synthesis of (R)-(-)-epinephrine

We report an in situ preparation of catalyst 3 which substantially simplifies the experimental procedure for the enantioselective, catalytic acetate aldol addition reaction. The addition of Me3SiCl and Et3N circumvents the azeotropic removal of the released isopropanol upon treating ligands 1 and 2 with Ti(O(i)Pr)4. Importantly, this new procedure maintains the salient features of the catalytic process we originally described: high yields and enantioselectivities, low catalyst loads, and convenient reaction times and temperatures. We have applied the new procedure to an efficient synthesis of (R)-(-)-epinephrine from commercially available reagents in an overall yield of 45%.