98104-30-4

Upstream product

• 14132-21-9 (-)-2-tert-butylcyclohexanone 
• 88-41-5 trans-2-tert-butylcyclohexyl acetate 
• 557088-93-4 (+)-3β-Acetoxy-Δ⁵-aetiensaeure-trans-2-tert.-butyl-cyclohexanolester 
• 7150-18-7 3β-acetoxyetienic acid 
• 5448-22-6 trans-2-tert-butylcyclohexan-1-ol 
• 3419-66-7 1-tert-butyl-1-cyclohexene 
• 108-94-1 cyclohexanone 
• 159425-79-3 (1S,2S,S_S)-2-tert-butyl-1-(N-tert-butyldiphenylsilyl-S-phenylsulfonimidoylmethyl)cyclohexanol 
• 1728-46-7 2-tert-butylcyclohexanone 
• 142798-18-3 trans-2-tert-Butylcyclohexylchloracetat 

Downstream Products

• 14132-21-9 (-)-2-tert-butylcyclohexanone 

Relevant academic research and scientific papers

Enantioselective Hydroazidation of Trisubstituted Non-Activated Alkenes

A one-pot procedure for the enantioselective hydroazidation of non-activated trisubstituted alkenes is described. Hydroboration with monoisopinocampheylborane (IpcBH2) provides dialkylboranes that are in situ selectively converted into monoalkyl-substituted catecholboranes; these undergo radical azidation upon treatment with benzenesulfonyl azide and a radical initiator. Enantiomerically enriched azides were thus obtained in yields of 59–81 % and enantioselectivities of up to 94:6 e.r. (98:2 e.r. if the intermediate dialkylborane is purified by crystallization). A rapid access to enantiomerically pure (+)-rodocaine is also described. The use of other arenesulfonyl radical traps enables enantioselective hydroallylation, hydrosulfanylation, and hydrobromination reactions with yields of 71–86 %.

Process for producing optically active compound

A process for producing an optically active compound based on the hydrolysis of an alkenyl ester compound or the cleavage of an alkenyl ether compound. The process uses neither an acidic compound nor a basic compound, and rectants can be reacted in a high concentration. It does not necessitate a buffer, nutrient, etc. unlike enzymatic reactions or reactions using a microorganism. It is a simple process which attains a satisfactory production efficiency. The process, which is for producing an optically active carboxylic acid or optically active alcohol represented by the general formula (VI): (wherein R1, R2, and R3 are different groups; and A represents methylene, carbonyl, or a single bound), is characterized by causing water to act on an alkenyl ester or alkenyl ether represented by the general formula (I): (wherein R4, R5, and R6 each represents hydrogen, alkyl, etc.) in the presence of a specific transition metal complex having an optically active ligand.

Amber-woody scent: Alcohols with divergent structure present common olfactory characteristics and sharp enantiomer differentiation

Only one out of the four possible trans isomers of the important perfumery alcohol Norlimbanol (1) possesses a very strong amber-woody smell, the isomer 1A with (1′ R,3S,6'S) absolute configuration. Its enantiomer 1B is almost odorless and devoid of amber-woody character, whereas the diastereoisomers 1C and 1D are considerably weaker and perceptible only by the most-sensitive persons. The same is true for a whole series of perceptual analogs of 1, including β-alkoxy alcohols. These ethers belong to two structural classes: [(2,2,6-trimethylcyclohexyl)oxy]- (see 3, 4, and 16) or {[2-(tert-butyl)cyclohexyl]oxy)alkan-2-ol derivatives (see 19 and 20; Table). A superimposition model allowing for good overlap of the respective hydroxylated side chains offers a tentative explanation for the shared perceptual characteristics of the two classes (Fig. 5). The lipophilic cyclohexane moieties present only a minimal overlap in this model, suggesting that quite larger molecules might possess the same smell. (S)-Configured β-alkoxy alcohols can conveniently be obtained on a larger scale by enantioselective reduction of the corresponding ketones (Scheme 9).

Effective nonenzymatic kinetic resolution of (±)-trans-2-arylcyclohexanols using 3β-acetoxyetienic acid, DCC, and DMAP

(1R,2S)-trans-2-Arylcyclohexanols of high enantiomerically purity were obtained by the simple stirring of the corresponding (±)-arylcyclohexanols with 3β-acetoxyetienic acid, DCC, and DMAP at room temperature.

Chiral Sulfur Compounds. Part 25. Diastereoselective 1,2-Additions of Lithiated (+)-(S)-N-tert-Butyldiphenylsilyl-S-methyl-S-phenylsulfoximine to Ketones

Lithiated (+)-(S)-N-tert-butyldiphenylsilyl-S-methyl-S-phenylsulfoximine 2f reacts with prochiral ketones to give a mixture of diastereomeric β-hydroxy sulfoximine adducts with a diastereoselection ranging from 79:21 to 98:2 depending upon the steric demand of the ketone.Racemic chiral cyclic ketones react with 2f to give a mixture of diastereoisomeric β-hydroxy sulfoximine adducts which could be separated by a combination of column chromatography and recrystallization.Thermolysis of the diastereoisomerically pure adducts gave 2-alkylcyclohexanones in high enantiomeric purity.The relative stereochemistries of four of the β-hydroxy sulfoximine adducts have been unequivocally determined from single-crystal X-ray structural analysis.The stereochemical outcome of these 1,2-additions can best be rationalized by invoking competing boat transition states.

LIPASE-CATALYZED ESTER FORMATION IN ORGANIC SOLVENTS. AN EASY PREPARATIVE RESOLUTION OF α-SUBSTITUTED CYCLOHEXANOLS

The commercial preparation "lipase My" catalyzes ester formation from an alcohol and a fatty acid in organic solvents.Preparative resolution of α-substituted cyclohexanols, including menthol, was achieved under these conditions.