214853-88-0

Upstream product

• 506-96-7 Acetyl bromide 
• 2043-61-0 cyclohexanecarbaldehyde 
• 132835-55-3 (+/-)-4-cyclohexyloxetan-2-one 
• 100-51-6 benzyl alcohol 
• 75-36-5 acetyl chloride 
• 463-51-4 Ketene 

Downstream Products

• 172376-40-8 (S)-1-cyclohexyl-1,3-propanediol 
• 279257-02-2 (R)-3-Amino-3-cyclohexyl-propionic acid methyl ester 
• 279257-01-1 (R)-3-cyclohexyl-3-(o-nitrobenzenesulfonamido)propionic acid methyl ester 
• 1026715-43-4 (R)-3-Cyclohexyl-3-(2-nitro-benzenesulfonylamino)-propionic acid 
• 279256-92-7 (R)-3-azido-3-cyclohexylpropanoic acid 

Relevant academic research and scientific papers

Catalytic asymmetric synthesis of trans-configured β-lactones: Cooperation of Lewis acid and ion pair catalysis

The development of the first trans-selective catalytic asymmetric [2+2] cyclocondensation of acyl halides with aliphatic aldehydes furnishing 3,4-disubstituted β-lactones is described. This work made use of a new strategy within the context of asymmetric dual activation catalysis: it combines the concepts of Lewis acid and organic aprotic ion pair catalysis in a single catalyst system. The methodology could also be applied to aromatic aldehydes and offers broad applicability (29 examples). The utility was further demonstrated by nucleophilic ringopening reactions that provide highly enantiomerically enriched anti-aldol products.

Symmetrie macrocycles by a prins dimerization and macrocyclization strategy

A tandem dimerization/macrocyclization reaction utilizing the Prins cyclization has been developed. This reaction develops molecular complexity through the formation of highly substituted dimeric tetrahydropyran macrocycles. Mild conditions utilizing rhen

Practical enantioselective synthesis of β-lactones catalyzed by aluminum bissulfonamide complexes

The development of an efficient and practical aluminum-bissulfonamide complex catalyzed enantioselective formation of β-lactones by [2+2] cycloaddition of ketene (generated in situ from acetyl bromide by dehydrobromination) with various α-unbranched and -

Enantioselective β-lactone formation from ketene and aldehydes catalyzed by a chiral oxazaborolidine

(Chemical Equation Presented) A novel catalytic system has been developed for the enantioselective synthesis of β-lactones from ketene and aldehydes.

Cinchona Alkaloid-Lewis Acid Catalyst Systems for Enantioselective Ketene-Aldehyde Cycloadditions

Asymmetric cinchona alkaloid-catalyzed acid chloride-aldehyde cyclocondensation (AAC) reactions afford enantioenriched 4-substituted and 3,4-disubstituted β-lactones with near perfect absolute and relative stereocontrol. These reactions are characterized

Synthesis and inhibitory action on HMG-CoA synthase of racemic and optically active oxetan-2-ones (β-Lactones)

A homologous series of both C3-unsubstituted and C3-methyl substituted oxetan-2-ones (β-lactones) was investigated as potential inhibitors of yeast 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) synthase. Several reported methods for racemic β-lactone synthesis were studied for preparation of the target series. In addition, a novel aluminum-based Lewis acid obtained by combination of Et2AlCl with (1R,2R)-2-[(diphenyl)hydroxymethyl] cyclohexan-1-ol was studied for the asymmetric [2+2] cycloaddition of aldehydes and trimethylsilylketene. This Lewis acid exhibited good reactivity but variable enantioselectivity (22-85% ee). In in vitro assays using both native and recombinant HMG-CoA synthase from Saccharomyces cerevisiae, oxetan-2-ones mono-substituted at C4 with linear alkyl chains gave IC50s that decreased monotonically with chain length up to 10 carbons and then rose rapidly for longer chains. The trans isomers of 3-methyl-4-alkyl-oxetan-2-ones showed a similar trend but had 1.3- to 5.6-fold lower IC50s. The results imply a substantial hydrophobic pocket in this enzyme that interacts with both C-3 and C-4 substituents of oxetan-2-one inhibitors. Copyright (C) 1998 Elsevier Science Ltd.

Studies of the asymmetric [2+2] cycloaddition of silylketenes and aldehydes employing Ti-TADDOL catalysts

Ti-TADDOL catalysts provide good reactivity and moderate enantioselectivity in the asymmetric [2+2] cycloaddition of silyl ketenes and aldehydes. The effects of potential bidentate chelation of benzyloxy substituted aldehydes and of the steric size of the ketene silyl group were studied.

Asymmetric Cycloaddition of Ketene with Aldehydes catalysed by Chiral Bissulfonamide-Trialkylaluminium Complexes

Asymmetric cycloaddition of ketene with the aldehydes 1a-g, catalysed by 10 molpercent of C2-symmetric bissulfonamide 2a-c-R3Al complexes afforded optically active 4-substituted oxetan-2-ones 3a-g in up to 74percent enantiomeric excess.