188593-96-6

Upstream product

• 101113-92-2 2-Phenyl-oxazolidine-4-spiro-cyclohexane 
• 100-52-7 benzaldehyde 
• 39692-17-6 1-amino-1-cyclohexane carboxylic acid hydrochloride 
• 4313-56-8 (1-aminocyclohexyl)methanol 

Downstream Products

• 188593-97-7 1-(Benzylideneamino)cyclohexanemethanol N-oxide 
• 188594-49-2 [1-((3aS,6S,6aR)-6-Cyclohexyl-tetrahydro-furo[3,4-c]isoxazol-1-yl)-cyclohexyl]-methanol 

Relevant academic research and scientific papers

Bicyclic and tricyclic compounds with β-amino alcohol groups as chiral ligands in the enantioselective reaction of diethylzinc with aldehydes

Reduction of the enantiomerically pure allyloxy esters 9 or ent-9 with DIBAH afforded the corresponding aldehydes which were treated in situ with chiral or achiral hydroxylamines 8 to give nitrones 10. These underwent a spontaneous intramolecular 1,3-dipolar cycloaddition, affording the bicyclic compounds 11 and 12, respectively. In an analogous manner, a mixture of the tricyclic compounds 14 and 15 was prepared. Treatment of compound 16 with cyclohexene oxide afforded a mixture of diastereomers 17 and 18. Diastereomers 14 and 15 as well as 17 and 18 could be separated by chromatography. X-ray analyses of compounds 11Ff, 17, and 11Af · HCI were performed. The bicyclic and tricyclic compounds were used as chiral ligands in the reaction of diethylzinc with aldehydes 19, in particular with benzaldehyde (19a). Using bicyclic compounds with a tertiary β-hydroxyalkyl substituent at the N atom as ligands, ee's in the range of 78 to 95% were found. Whereas for the best ligands 11Ae and Af the enantioselectivity in the reaction of 4-tolualdehyde was only slightly decreased, with the aliphatic aldehydes 19c and d distinctly lower enantioselectivities were determined. VCH Verlagsgesellschaft mbH, 1997.

5,6,7-Trinor-4,8-inter-m-phenylene prostaglandin I2 derivatives useful in anti-ulcer, hypotensive and platelet aggregation inhibiting compositions

A compound of the formula STR1 wherein R1 is a pharmaceutically acceptable cation, hydrogen or n-alkyl of 1 to 12 carbon atoms; R2 is hydrogen, acyl of 2 to 10 carbon atoms or aroyl of 7 to 13 carbon atoms; R3 is hydrogen, acyl of 2 to 10 carbon atoms or aroyl of 7 to 13 carbon atoms; R4 is hydrogen, methyl or ethyl; R5 is n-alkyl of 1 to 5 carbon atoms; n is an integer of 0 to 4; A is --CH2 --CH2 -- or trans --CH=CH--; and X is --CH2 --CH2 -- or trans --CH=CH--. The compounds are useful in anti-ulcer, hypotensive and platelet aggregation inhibiting compositions.