186763-30-4

Upstream product

• 1027301-94-5 (2S,5R)-5,6-Dihydroxy-2-isopropyl-2-phenyl-hexanenitrile 
• 458557-61-4 (R)-2-Formyl-3-methyl-2-phenyl-butyronitrile 
• 350795-06-1 (2R)-2-hydroxymethyl-2-isopropyl-2-phenylacetonitrile 
• 350795-03-8 (2S,3S)-3-isopropyl-2-phenyl-2,3-epoxypropan-1-ol 
• 350795-07-2 ethyl (4R)-4-cyano-4-phenyl-5-methyl-trans-hex-2-enoate 
• 318969-12-9 ethyl (4S)-4-cyano-4-phenyl-5-methylhexanoate 
• 350795-05-0 (S)-3-methyl-2-phenyl-2-((triphenylsilyloxy)methyl)butanal 
• 350795-04-9 (2S,3S)-3-isopropyl-2-phenyl-2,3-epoxypropan-1-triphenylsilyl ether 
• 5558-29-2 3-methyl-2-phenyl-butyronitrile 
• 186763-23-5 (S)-3-cyano-4-methyl-3-phenylpentanal 
• 350795-08-3 (2S)-2-(2-isopropyl)-5-hydroxy-2-phenylpentanenitrile 

Downstream Products

• 350795-08-3 (2S)-2-(2-isopropyl)-5-hydroxy-2-phenylpentanenitrile 
• 493006-79-4 (S)-4-cyano-5-methyl-4-phenylhexyl mesylate 

Relevant academic research and scientific papers

Enantioselective synthesis of nitriles containing a quaternary carbon center by michael reactions of silyl ketene imines with 1-acrylpyrazoles

The enantioselective construction of quaternary carbon centers is a marked challenge in asymmetric catalysis research. It is extremely difficult when a chiral catalyst can not distinguish the facial selectivity of the substrate through bond interactions. Here we realized an enantioselective Michael reaction of silyl ketene imines to 1-acrylpyrazoles using a chiral N,N′-dioxide-Co(II) complex. The protocol is highly efficient for the construction of nitrile-, aryl-, and dialkyl-bearing carbon centers and has been successful applied in the divergent synthesis of pharmaceuticals and natural products. The through-space dispersion interactions between unbound silyl ketene imines and the 1-acrylpyrazole-bonded catalyst play a key role in facilitating the reactivity and the enantioselectivity of this process.

Practical synthesis of chiral emopamil left hand as a bioactive motif.

An asymmetric synthesis of (2S)-2-(2-isopropyl)-5-hydroxy-2-phenylpentanenitrile (emopamil left hand, 2) has been completed by use of the MAD (methyl aluminum bis(4-methyl-2,6-di-tert-butylphenoxide)-induced rearrangement of a chiral epoxyalcohol as the key reaction. The stereochemistry of the chiral quaternary center was confirmed by transformation of 2 to (S)-noremopamil. This method requires minimal purification procedures and affords high chemical and optical yields. Acid-catalyzed isomerization of an allylaldehyde and retro-aldol type racemization at the quaternary carbon of a nitrile-alcohol were encountered.

Novel N-substituted alpha aminoacid amides as calcium channel modulators

The compounds of formula I and derivatives thereof have been found to be active in tests that show modulation of voltage-dependent calcium channels, and are thus indicated for use in the treatment of diseases in which such modulation is beneficial, in par

Convenient synthesis of (2R)- and (2S)-2-(1-methylethyl)-5-oxo-2-phenylpentanenitrile, intermediates in the preparation of phenylalkylamine calcium channel blockers

The multigram synthesis of (2S)- and (2R)-2-(1-methylethyl)-5-oxo-2-phenylpentanenitriles 9a and 9b is described, using either (4,R)-2,2-dimethyl-1,3-dioxolan-4-ylmethanol or (2R)-butane-1,2,4-triol as chiral auxiliary. The configuration of an intermediate dioxolane 10b is assigned by X-ray crystallography. The synthetic utility of the aldehydes is demonstrated by conversion to both enantiomers of the calcium antagonist noremopamil in >98% enantiomeric excess (ee). The enantiomeric purity of the final amines is assayed by 1H NMR spectroscopy in the presence of the chiral solvating agent (1R)-(-)-2,2,2-trifluoro-1-(9-anthryl)ethanol.