• Korean Chemical Engineering Research
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• v.43 no.6
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• pp.647-661
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• 2005

The stereoselective synthesis of chiral terminal epoxide is of immense academic and industrial interest due to their utility as versatile starting materials as well as chiral intermediates. In this review, we investigate the research and development trend in the asymmetric ring opening reactions using cobalt salen catalysts. Hydrolytic kinetic resolution (HKR) technology is the very prominent way to prepare optically pure terminal epoxides among available methods. We have synthesized homogeneous and heterogeneous chiral dinuclear salen complexes and demonstrated their catalytic activity and selectivity for the asymmetric ring opening of terminal epoxides with variety of nucleophiles and for asymmetric cyclization to prepare optically pure terminal epoxides in one step. The resolved ring opened product combined with ring closing in the presence of base and catalyst afforded the enantioriched terminal epoxides in quantitaive yield. Potentially, these catalysts are using on an industrial scale to produce chiral intermediates. The experimental results of HKR technology applied to the synthesis of various chiral compounds are presented in this paper.

• Bulletin of the Korean Chemical Society
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• v.23 no.11
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• pp.1611-1615
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• 2002

The ring opening of epoxides with elemental iodine and bromine in the presence of three diamine podands 7-9 as new catalysts affords vicinal iodo alcohols and bromo alcohols in high yields. This new procedure occurs regioselectively under neutral and mild conditions in various aprotic solvents even when sensitive functional groups are presented.

• Archives of Pharmacal Research
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• v.14 no.2
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• pp.143-146
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• 1991

A new synthetic sequence for the chiral lactone moiety of compactin was developed from $\alpha$-D-glucose in 9 steps via simultaneous reductive detosylation and epoxide-ring opening of 2, 3-epoxy-4-tosylate using NaBH_4$ to afford 2, 4-dideoxy sugar as a key intermediate.

• Bulletin of the Korean Chemical Society
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• v.34 no.4
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• pp.1247-1249
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• 2013

• Bulletin of the Korean Chemical Society
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• v.17 no.9
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• pp.831-835
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• 1996

New dynemicin A mimics with methyl group 2a and 2b were synthesized, and acid-induced hydrolyzed to see an electronic effect of substituent for epoxide opening. The model 2a with methyl group at C3 position was more rapidly transformed to diol 16a than 2b with methyl group at C2. This result suggests that any substituent at C3 position plays more important role than any substituent at C2 position in the dynemicin A mimic activation.

• Bulletin of the Korean Chemical Society
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• v.28 no.9
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• pp.1553-1561
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• 2007

The new type of heterometallic chiral polymer salen complexes have been synthesized and it has been found that group 13 metal salts (AlCl3, GaCl3 and InCl3) combined to cobalt salen unit played the crucial role in the asymmetric kinetic resolution of racemic epoxides. Polymeric salen catalysts showed very high reactivity and enantioselectivity for the asymmetric ring opening of terminal epoxide with diverse nucleophiles. They provide the enantiopure useful chiral intermediates such as chiral terminal epoxides and α -aryloxy alcohols in one-step process. An efficient methodology for providing very high enantioselectivity can be achieved in the synthesis of valuable chiral building blocks via our catalytic system by combination of various asymmetric ring opening reactions.

• Bulletin of the Korean Chemical Society
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• v.31 no.10
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• pp.2973-2979
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• 2010

The newly synthesized homogeneous chiral Co(III) salen complexes were anchored non-covalently on the acidic sites of mesoporous Al-SBA-15. The Bronsted and Lewis acidic sites are attributed to the immobilization of fluorine functionalized chiral salen complexes on the supports. XRD, BET, TEM, FT-IR and ESCA (XPS) analyses were performed to characterize the property of support, and the structure of new homogeneous and heterogeneous chiral Co salen catalyst. The homogeneous and heterogeneous catalysts could be applied in asymmetric ring opening of epichlorohydrine (ECH) by water. They showed very high enantioselectivity and a good yield up to 99% in the catalytic synthesis of optically active products.

• Bulletin of the Korean Chemical Society
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• v.30 no.1
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• pp.163-171
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• 2009

Few $\alpha$-Hydroxy-$\beta$-amino acids were synthesized via various nucleophilic addition of the epoxide and followed by stereoselective nucleophilic substitution reaction and eliminative cleavage of the acetal selectively in diacetal compound. One of the synthesized $\alpha$-Hydroxy-$\beta$-amino acid reacted with L-leucine methylester to give corresponding dipeptide in good yields.

• Applied Chemistry for Engineering
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• v.18 no.2
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• pp.116-120
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• 2007

The synthesis of 1-[2-(3-{7-oxabicyclo[4.1.0]heptyl} 1,1,3,3-tetramethyl-disiloxane (Mono), which is a key intermediate for the synthesis of monomers applied for photopolymer systems based on the cationic ring opening polymerization, was studied. Mono was successfully synthesized by the hydrosilylation reaction of 4-vinyl-1-cyclohexene 1,2-epoxide (VCHO) with an excess amount of 1,1,3,3-tetramethyldisiloxane (TMDS) in the presence of a Speier catalyst. The structure and the purity of Mono were characterized by FT-IR, $^1H-NMR$, and $^{29}Si-NMR$. The optimum conditions for the hydrosilyation reaction were found to be 1:4 molar ratio of VCHO to TMDS and 5 ppm of the catalyst at the temperature of $55^{\circ}C$.

• Bulletin of the Korean Chemical Society
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• v.32 no.spc8
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• pp.2965-2969
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• 2011

Highly efficient and rapid aminolysis of epoxides with various amines in water under microwave irradiation in the absence of catalyst was developed. Chiral ${\beta}$-amino alcohols were formed in a short time with excellent yields.