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Jin Soon Cha, Seung Jin Park 조선대학교 기초과학연구원 2009 조선자연과학논문집 Vol.2 No.3
The new MPV-type reagent, Al-fluorodiisobutylalane (DIBAF), has been prepared and their reducing characteristics in the reduction of selected organic compounds containing representative functional groups have been examined in order to find out a new reducing system with unique applicability in organic synthesis. In general, the reagent is extremely mild, showing only reactivity toward aldehydes, ketones, and epoxides. The reagent achives a clean 1,2-reduction of enals to the corresponding allylic alcohols in a 100% purity, but shows no reactivity toward enones. The reagent also shows an excellent regioselective cleavage of substituted epoxides. In addition, DIBAF produces the thermodynamically more stable alcohol epimer in high stereoselectivity in the reduction of cyclic ketones
Diisobutyldiethylaminoalane에 의한 카르보닐 화합물의 선택환원
차진순 嶺南大學校 基礎科學硏究所 1995 基礎科學硏究 Vol.15 No.-
The reducing characteristics of diisobutyldiethylaminoalane, as a chemoselective reducing agent in the reduction of an equimolar amount of different carbonyl compounds, have been examined systematically. Aldehydes are smoothly reduced to alcohols. Furthermore, conjugated aldehydes and ketones are reduced to the corresponding allylic alcohols quantitatively by diisobutyldiethylaminoalane in ether solution with excellent purity.
차진순,이재철 嶺南大學校基礎科學硏究所 1999 基礎科學硏究 Vol.19 No.-
The reducing characteristics of diisobutyldiphenylaminoalane (DIBANPh_2) as selective reducing agent in the reduction of carbonyl compounds, have been studie systematically. Aldehydes are smoothly reduced to the corresponding alcohols by BIBANPh_2 i ether solution.
키랄성 Oxazaborolidine과 Thexylborane을 이용한 대표적인 케톤의 비대칭환원
차진순 嶺南大學校 基礎科學硏究所 1997 基礎科學硏究 Vol.17 No.-
The asymmetric reduction of aromatic and aliphatic ketones with thexylborane(ThxBH₂) complexed with chiral oxazaborolidine prepared from the reaction of (S)-(-)-2-(diphenylhydroxymethyl)pyrrolidine and borane has been investigated in order to characterize the role of boron hydride reagent in asymmetric induction. The reduction of acetophenone yields(R)-1-phenylethanol in 63.8%ee by ThxBH₂-BAMDPB. Branching of the alkyl chain increased the induction. Thus, propiphenone and butyrophenone were reduced to the corresponding alcohols in 76.0%ee, 78.2%ee, respectively. The reductio of aliphatic ketones also provided the corresponding (R)-alcohols. The asymmetric induction in the reaction of 3-methyl-2-butanone, 3,3-dimethyl-2-butanone, 4,4-dimethyl-2-pentanone were 80.5%ee, 82.6%ee, 87.6%ee, respectively. In general, the asymmetric inducibility by the system is significantly lower than that achieved by the BH₃system. Apparently, the higher steric hinderance of ThxBH₂than that of BH₃seems to inhibit the coordination of these boranes to oxazaborolidine to result in the lower asymmetric induction.
BH₃와 PCC를 이용하여 환원-산화법에 의한 카르복시산 염으로부터 알데히드 합성에 관한 연구
차진순, 이재철 영남대학교 기초과학연구소 2000 基礎科學硏究 Vol.20 No.-
A new convinent conversion of carboxylic acid salts into the corresponding aldehydes by utilizing borane has been devised : the procedure involves the reaction of carboxylic acid salts with borane to form the acyloxyborohydride intermediate, followed by the treatment with dimethyl sulfate to be converted into trialkoxyboroxine. Finally, the boroxine intermediate is converted to aldehydes by oxidation with pyridinium chlorochromate or pyridinium dichromate. The yields of aldehydes by this procedure are very excellent. This method provides one of the most economical procedures reported in the literature.
디이소부틸수소화알루미늄=메틸설피드 착물에 의한 니트릴의 알데히드로의 환원
車震淳 嶺南大學校 基礎科學硏究所 1993 基礎科學硏究 Vol.13 No.-
A systematic study of the partial reduction of nitriles to the corresponding aldehydes with diisobutylaluminum hydride-dimethyl sulfide complex under practical conditions has been carried out. The yields of aldehydes are good in the aliphatic and aromatic series.
텍실브로모보란-메틸 설피드 착물을 이용한 카르복시산의 알데히드로의 부분 환원
차진순,윤말숙,김진억,오세연 嶺南大學校附設 基礎科學硏究所 1985 基礎科學硏究 Vol.5 No.-
The systematic study on the direct partial reduction of carboxylic acids to the corresponding aldehydes with thexylbromoborane-methyl sulfide under the practical conditions (carbon disulfide, room temperature) has been done and also some representative carboxylic acids have been applied to the partial reduction under the optimal reaction condition. The reaction is quite general and the yields of aldehydes are very excellent, especially almost quantitative in aliphaticcarboxylic acids.
9-텍실옥실-9보라타비시클로[3. 3. 1]노난 리튬의 합성과 그것의 입체선택환원성
車震淳,金進億,金鍾大 嶺南大學校附設 基礎科學硏究所 1984 基礎科學硏究 Vol.4 No.-
The reaction in tetrahydrofuran of potassium 9-(2,3-dimethyl-2-butoxy)-9-boratabicyclo [3. 3. 1]nonane (K 9-OThx-9-BBNH) with lithium chloride was examined in detail to establish the generality of this synthesis of the corresponding lithium derivatives. This new reagent, Li 9-OThx-9-BBNH, shows an excellent stereoselectivity .in the reduction of cyclic ketones. Especially, the easy removal of the byproduct of the reaction and thus simple isolation procedure provides a major advantage for this reagent.
트리알콕시수소화붕소 리튬의 합성과 그들의 안정성 및 화학
車震淳,金進億,李在哲 嶺南大學校附設 基礎科學硏究所 1984 基礎科學硏究 Vol.4 No.-
The reaction in tetrahydrofuran of potassium trialkoxyborohydrides with lithium chloride was examined in detail to establish the generality of this synthesis of the corresponding lithium trialkoxyborohydrides and the stability of these lithium derivatives in tetraydrofuran was examined using ?? NMR spectroscopy. For R=i-Pr, the lithium salt is very stable. However, R=s-Bu and t-Bu, with increasing steric requirement, the lithium derivatives are unstable and thus dissociated into (RO)BH₃- and (RO)₄B-. The stereoselectivity of lithium triisopropoxyborohydride (LIPBH) on the reduction of cyclic ketones was investigated and compared with that of the potassium derivative.