86504-11-2Relevant articles and documents
Catalytic behaviour of chloroperoxidase from Caldariomyces fumago in the oxidation of cyclic conjugated dienes
Sanfilippo, Claudia,Nicolosi, Giovanni
, p. 1889 - 1892 (2007/10/03)
Chloroperoxidase from Caldariomyces fumago has been investigated as a catalyst for the oxidation of cyclic conjugated dienes. The nature of the substituents and the size of the carbocycle affect the enantioselectivity of the enzyme. An unexpected course o
Enzymatic Access to Homochiral 1-Acetoxy-2-hydroxycyclohexane-3,5-diene through Lipase-assisted Acetylation in Organic Solvent
Nicolosi, Giovanni,Patti, Angela,Piattelli, Mario,Sanfilippo, Claudia
, p. 6545 - 6546 (2007/10/02)
Enantiotoposelective acetylation of cis-1,2-dihydroxycyclohexa-3,5-diene with vinyl acetate in tert-butyl methyl ether, promoted by immobilized lipase from Mucor miehei (Lipozyme IM), afforded (1R,2S)-1-acetoxy-2-hydroxycyclohexa-3,5-diene in good chemical yield and high enantiomeric excess.
Highly enantio- and diastereo-selective synthesis of C2-symmetric 3,5-cyclohexadiene-1,2-diol and D2-symmetric cyclohexane-1,2,4,5-tetrol
Suemune,Hasegawa,Sakai
, p. 55 - 58 (2007/10/02)
Highly enantio- and diastereo-selective synthesis of C2-symmetric 3,5-cyclohexadiene-1,2-diol 5 and D2-symmetric cyclohexane-1,2,4,5-tetrol related compounds 7a,b 10, 11 has been achieved using optically active 4-cyclohexene-1,2-diol
?-Facial diastereoselectivity in the Diels-Alder reactions of cis-cyclohexa-3,5-diene-1,2-diol and derivatives with N-phenylmaleimide
Gillard, James R.,Burnell, D. Jean
, p. 1296 - 1307 (2007/10/02)
N-Phenylmaleimide undergoes Diels-Alder cycloaddition predominantly to the face of cis-cyclohexa-2,4-diene-1,2-diol (3) syn to the oxygen functions.Derivatization can be used to alter the ?-facial diastereoselectivity in a synthetically useful manner.The
Synthesis of N-Acetyl-D- and -L-glucosamine, cis-3,5-Cyclohexadiene-1,2-diol as Building Block for the Preparation of Modified Hexoses
Lehmann, Jochen,Moritz, Andreas
, p. 937 - 940 (2007/10/02)
Six-membered, unsaturated carbocycles are versatile starting materials for the preparation of a large variety of modified hexoses.This is exemplified by the synthesis of N-acetylglucosamine 12 as a racemate from cis-3,5-cyclohexadiene-1,2-diol (1), which can be obtained by microbial oxidation of benzene.In this special case D- and L-N-acetylglucosamine could be differentiated by enzymatic D-galactosylation of the former. Key Words: Microbial oxidation / Epoxides / Ozonolysis / Hemiacetals / Transgalactosylation, enzymatic
Asymmetric Induction of Four Chiral Centers by Hetero Diels-Alder Reaction of a Chiral Nitroso Dienophile
Werbitzky, Oleg,Klier, Konrad,Felber, Helena
, p. 267 - 270 (2007/10/02)
The Diels-Alder reaction of cis-5,6-diacetoxy-1,3-cyclohexadiene (1), which has a meso configuration, with the chiral nitroso dienophile 2 occurs with induction of four asymmetric centers in very high optical yield (ee = 94percent) and leads to the dihydr
Mikrobial Oxidation in Synthesis: Preparation of (+)- and (-)-Pinitol from Benzene
Ley, Steven V.,Sternfeld, Francine
, p. 3463 - 3476 (2007/10/02)
Microbial oxidation with Pseudomonas putida of benzene affords cis-1,2-dihydroxycyclohexa-3,5-diene (2) which may be converted in five steps and 49percent overall yield to (+/-)-pinitol.Resolution of an intermediate alcohol (6) with menthoxyacetyl chloride provides optically pure materials which may be independently transformed to (+)- or (-)-pinitol.Demethylation conditions for pinitol together with further reactions of (2) and related compounds were investigated.
Resolution of trans-1,2-Dihydroxy-1,2-dihydrobenzene for the Preparation of Optically Pure Benzene Diol Epoxides. Preparation of Bromo- and Chlorobenzene Diol Epoxides
Ganey, Michael V.,Padykula, Robert E.,Berchtold, Glenn A.,Braun, Andrew G.
, p. 2787 - 2793 (2007/10/02)
The resolution of (+/-)-trans-1,2-dihydroxy-1,2-dihydrobenzene has been accomplished by esterase-catalysed hydrolysis of diacetate (+/-)-5.Peracid epoxidation of (+)-2 and (-)-2 gave diol epoxides (+)-3 and (-)-3, respectively.The synthesis of d