32908-36-4Relevant academic research and scientific papers
Method for synthesizing chiral amine compound
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Paragraph 0064; 0071-0073; 0129-0131, (2019/10/01)
The present invention provides a method for synthesizing a chiral amine compound. The method comprises the following steps: (1) reacting a compound of formula I with t-butylsulfonamide in the presenceof a catalyst to obtain a compound having a structure represented by formula II; 2) reacting the compound of the formula II in a hydrogen atmosphere in the presence of an iridium catalyst and a ligand to obtain a compound of formula III; and (3) carrying out a t-butylsulfonyl group removal reaction on the compound of the formula III to obtain the chiral amine compound. The method constructs the structure of sulfonamide by a keto carbonylgroup, and synthesizes the chiral amine compound with the aralkylamine structure by an asymmetric catalytic hydrogenation reaction of the sulfonamide structure, the ee value is generally 80% or above, the highest ee value is 99% or above, the yield of each step reaction can reach 90% or above, and the total yield is high.
Method for synthesizing dextral alpha-cyclohexylbenzylamine
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Paragraph 0008; 0011, (2017/07/01)
The invention discloses a method for synthesizing dextral alpha-cyclohexylbenzylamine. The method comprises synthesizing racemic alpha-cyclohexylbenzylamine through catalytic reduction of cyclohexyl phenyl ketone in the presence of a reduction catalyst, and carrying out dynamic kinetic resolution on alpha-cyclohexylbenzylamine under combined action of lipase and a racemization catalyst to obtain alpha-cyclohexylbenzylamine. The method has the characteristics of simple operation, wide raw material source, good product yield and high optical purity of the resolution product.
A versatile Ru catalyst for the asymmetric transfer hydrogenation of both aromatic and aliphatic sulfinylimines
Pablo, Oscar,Guijarro, David,Kovacs, Gabor,Lledos, Agusti,Ujaque, Gregori,Yus, Miguel
, p. 1969 - 1983 (2012/03/26)
A highly efficient Ru catalyst based on an achiral, very simple, and inexpensive amino alcohol ligand (2-amino-2-methylpropan-1-ol) has been developed for the asymmetric transfer hydrogenation (ATH) of chiral N-(tert-butylsulfinyl)imines. This complex is able to catalyze the ATH of both aromatic and the most challenging aliphatic sulfinylimines by using isopropyl alcohol as the hydrogen source. The diastereoselective reduction of aromatic, heteroaromatic, and aliphatic sulfinylketimines, including sterically congested cases, over short reaction times (1-4 h), followed by desulfinylation of the nitrogen atom, affords the corresponding highly enantiomerically enriched (ee up to >99%) α-branched primary amines in excellent yields. The same ligand was equally effective for the synthesis of both (R)- and (S)-amines by using the appropriate absolute configuration in the iminic substrate. DFT mechanistic studies show that the hydrogen-transfer process is stepwise. Moreover, the origin of the diastereoselectivity has been rationalized.
Synthesis of highly enantiomerically enriched amines by the diastereoselective addition of triorganozincates to N-(tert-butanesulfinyl)imines
Almansa, Raquel,Guijarro, David,Yus, Miguel
experimental part, p. 2484 - 2491 (2009/04/11)
The reaction of triorganozincates with (R)-N-(tert-butanesulfinyl) imines gives the expected α-branched sulfinamides in good to excellent yields with diastereomeric ratios of up to 98:2. The N-sulfinyl group of the products can be easily removed by acidic treatment, affording the corresponding chiral primary amines in enantiomeric excesses of up to 96%. The reactivity and the selectivity shown by the triorganozincates are different from the ones observed with the corresponding Grignard reagents, which allows, in several cases, the preparation of both enantiomers of an amine from the same imine substrate. When mixed triorganozincates are used, one can take advantage of the slow transfer rate of the methyl group to use it as a non-transferable one. Both aromatic and aliphatic aldimines, as well as activated ketimines, are good substrates for these addition reactions.
Chiral oxime ethers in asymmetric synthesis. Part 4. Asymmetric synthesis of N-protected amines and β-amino acids by the addition of organometallic reagents to ROPHy/SOPHy-derived aldoximes
Hunt, James C. A.,Lloyd, Cephas,Moody, Christopher J.,Slawin, Alexandra M. Z.,Takle, Andrew K.
, p. 3443 - 3454 (2007/10/03)
Addition of organolithium or Grignard reagents to (R)- or (S)-O-(1-phenylbutyl)aldehyde oximes 1 in the presence of boron trifluoride-diethyl ether results in the formation of hydroxylamines 2 in good to excellent diastereoselectivity. Subsequent cleavage of the N-O bond with zinc-acetic acid-ultrasound, and carbamate formation, gives N-protected amines 3 in good enantiomeric purity (77-100% ee). When allylmagnesium bromide was used as the organometallic reagent, the resulting hydroxylamines were converted into β-amino acid derivatives 4 and γ-aminb alcohols 5. The Royal Society of Chemistry 1999.
ASYMETRIC SYNTHESIS X: THE HIGH ENANTIOSELECTIVE SYNTHESIS OF (R)-α-SUBSTITUTED BENZYLIC AMINES VIA THE MODIFIED (+)-CAMPHOR DERIVATIVE AS CHIRAL SYNTHON
Yaozhong, Jiang,Peng, Guo,Guilan, Liu
, p. 15 - 22 (2007/10/02)
A new chiral synthon-10-substituted (+)-camphor derivative (III) is synthesized.The alkylation of the (III) with a variety of alkylating agents gives the high enantioselectivity ranging from 72-100percent e.e..And the crystal structures of the (III) and (IV) are involved in explaining the results.
ASYMMETRIC SYNTHESIS VIII: ENANTIONSELECTIVE SYNTHESIS OF (R) OR (S)-α-SUBSTITUTED BENZYLAMINES VIA CHIRAL PINANONE KETIMINE TEMPLATE
Yuanwei, Chen,Aiqiao, Mi,Xun, Xiao,Yaozhong, Jiang
, p. 1423 - 1430 (2007/10/02)
An excellent asymmetric synthesis of both (R) and (S)-α-substituted benzylamines in optical purity 90.4 - 99.9percent has been achieved by alkylation of a chiral ketimine, prepared from pinanone and benzylamine.Diastereoselectivity in the alkylation is not dependent on the alkyl halides.
