192060-34-7

Upstream product

• 90-82-4 pseudoephedrine 
• 108-12-3 isopentanoyl chloride 

Downstream Products

• 178871-92-6 (S)-2-benzyl-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-3,N-methylbutyramide 
• 196706-16-8 (E)-(S)-6-Cyclohexyl-2-isopropyl-hex-4-enoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide 
• 934841-37-9 C₃₄H₅₀N₂O₄ 
• 1015422-31-7 (S)-2-ethyl-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N,3-dimethylbutyramide 
• 1015422-36-2 (S)-2-isopropylpentanoic acid N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methyl amide 
• 1015422-15-7 (S)-2-isopropyl-5-methylhex-5-enoic acid N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methyl amide 
• 1015422-21-5 (S)-2-isopropyl-5-methylhex-4-enoic acid N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methyl amide 
• 1243333-16-5 (R)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,3-dimethyl-2-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)butanamide 
• 118832-53-4 (3S,5R)-5-((S)-1-Bromo-2-cyclohexyl-ethyl)-3-isopropyl-dihydro-furan-2-one 
• 118832-55-6 5-Bromo-6-cyclohexylmethyl-3-isopropyl-tetrahydro-pyran-2-one 
• 118041-14-8 5(R)-bromo-6-cyclohexyl-2(S)-isopropyl-4(S)-hexanolide 
• 324763-47-5 (2S,4S,5S,7S)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-5-azido-4-hydroxy-2-isopropyl-7-(4-methoxy-3-(methoxypropoxy)benzyl)-8-methylnonanamide 
• 387353-75-5 4-Bromo-benzenesulfonic acid (1R,3S)-1-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl ester 
• 324763-46-4 (3S,5S)-5-{(1S,3S)-1-azido-3-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-4-methylpentyl}-dihydro-3-(1-methylethyl)furan-2(3H)-one 

Relevant academic research and scientific papers

Electrophilic rearrangements of chiral amides: A traceless asymmetric α-allylation

A one-pot protocol for the asymmetric α-allylation reaction is reported relying on a key efficient asymmetric Claisen rearrangement, triggered by electrophilic activation of chiral pseudoephedrine amides. Subsequent reduction or hydrolysis of the resulting iminium ions provides highly enantioenriched α-allylic aldehydes or carboxylic acids in a traceless manner. Compared to traditional alternatives which make use of strongly basic conditions, the work presented herein displays unprecedented functional group tolerance.

Enantioselective synthesis of 2-substituted alcohols using (+)-(1S,2S)-pseudoephedrine as chiral auxiliary

An improved method for the selective synthesis of enantiopure 2-substituted alcohols is described. Highly diastereoselective alkylation of pseudoephedrine-derived amides and subsequent oxidation of the hydroxyl group in the amide side chain, leads to oxoamides. These oxoamides can be purified by crystallization or preparative HPLC to obtain diastereomeric ratios of >99:1. The following reductive cleavage of the modified auxiliary allows the epimerization-free formation of enantiopure 2-substituted alcohols with up to 99.9% ee. Georg Thieme Verlag Stuttgart.

Total synthesis of polyoxygenated cembrenes

(Chemical Presented) A convergent approach for the stereoselective construction of polyoxygenated cembrenes is reported. Key steps in the synthesis are an asymmetric domino multicomponent allylation, a modified Myers a-alkylation, and a ring-closing metathesis.

Pseudoephedrine as a practical chiral auxiliary for the synthesis of highly enantiomerically enriched carboxylic acids, alcohols, aldehydes, and ketones

The use of pseudoephedrine as a practical chiral auxiliary for asymmetric synthesis is described in full. Both enantiomers of pseudoephedrine are inexpensive commodity chemicals and can be N-acylated in high yields to form tertiary amides. In the presence of lithium chloride, the enolates of the corresponding pseudoephedrine amides undergo highly diastereoselective alkylations with a wide range of alkyl halides to afford α-substituted products in high yields. These products can then be transformed in a single operation into highly enantiomerically enriched carboxylic acids, alcohols, aldehydes, and ketones.