92685-83-1Relevant articles and documents
A convenient method for preparation of α-imino carboxylic acid derivatives and application to the asymmetric synthesis of unnatural α-amino acid derivative
Inokuma, Tsubasa,Jichu, Takahisa,Nishida, Kodai,Shigenaga, Akira,Otaka, Akira
, p. 573 - 581 (2019/12/26)
We describe herein a manganese(IV) oxide-mediated oxidation of N-p-methoxyphenyl (PMP)-protected glycine derivatives for the synthesis of α-imino carboxylic acid derivatives. Using this methodology, utilization of unstable glyoxic acid derivatives was avo
Derivatives and application to the asymmetric synthesis of unnatural α-amino acid derivative
Inokuma, Tsubasa,Jichu, Takahisa,Nishida, Kodai,Shigenaga, Akira,Otaka, Akira
, p. 573 - 581 (2017/06/07)
We describe herein a manganese(IV) oxide-mediated oxidation of N-p-methoxyphenyl (PMP)-protected glycine derivatives for the synthesis of a-imino carboxylic acid derivatives. Using this methodology, utilization of unstable glyoxic acid derivatives was avoided. Furthermore, using this methodology we synthesized novel a-imino carboxylic acid derivatives such as a-imino phenyl ester, perfluoroalkyl etsers, imides, and thioester. The asymmetric Mannich reaction of those novel imine derivatives with 1,3-dicarbonyl compound is also described, and the novel a-imino imide gave improved chemical yield and stereoselectivity compared with those obtained by the use of the conventional a-imino ester-type substrate.
Copper Triflate Catalyzed Oxidative α-Allylation of Glycine Derivatives
Chen, Ting-Ting,Cai, Chun
supporting information, p. 1368 - 1372 (2017/06/27)
Copper triflate catalyzed oxidative C-H functionalization of glycine derivatives with allyltributyltin has been established using oxygen or tert -butyl hydroperoxide as oxidant. Various glycine esters and glycine amides were suitable substrates for this oxidative allylation reaction and afforded the desired homoallylic amines in moderate to good yields.
Cross-dehydrogenative coupling reactions by transition-metal and aminocatalysis for the synthesis of amino acid derivatives
Xie, Jin,Huang, Zhi-Zhen
supporting information; experimental part, p. 10181 - 10185 (2011/02/27)
The direct approach: The title coupling reactions of N-aryl glycine esters with unmodified ketones occurred smoothly in the presence of tert-butyl hydroperoxide (TBHP) or 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) under mild conditions (see scheme). The oxidant used for C-H activation determined the selectivity of the reactions for a particular type of ketone substrate. Copyright
Palladium-catalyzed reactions in aqueous media. An efficient removal of allyloxycarbonyl protecting group from oxygen and nitrogen
Genet, Jean Pierre,Blart, Errol,Savignac, Monique,Lemeune, Stephane,Paris, Jean-Marc
, p. 4189 - 4192 (2007/10/02)
The Allyloxycarbonyl (Alloc) moiety can be removed smoothly and selectively in good yield (70-99%) from allylic esters, carbamates and carbonates by aqueous Pd (0) catalyzed allyl transfer to diethylamine as the accepting nucleophile. The method has been successfully used for deprotection of a wide range of secondary amines.
Dirhodium Tetraacetate Catalyzed Carbon-Hydrogen Insertion Reaction in N-Substituted α-Carbomethoxy-α-diazoacetanilides and Structural Analogues. Substituent and Conformational Effects
Wee, Andrew G. H.,Liu, Baosheng,Zhang, Lin
, p. 4404 - 4414 (2007/10/02)
A series of acyclic α-carbomethoxy-α-diazoacetanilides with different N-substituents, 5a-k, was prepared and the rhodium(II) acetate catalyzed reaction studied.It was found that the rhodium carbenoid reaction with these compounds occurred only at the N-substituent; when the N-substituent is a propargyl group, rhodium carbenoid addition to the triple bond is favored, resulting, ultimately, in the formation of a bicyclic furan derivative 8.With an N-(tert-butyloxycarbonyl)methyl substituent, interception of the rhodium carbenoid by the ester carbonyl oxygen occurred preferentially to give, eventually, 1,4-oxazine derivatives 9 and 9'.For N'-alkyl substituents, rhodium carbenoid carbon-hydrogen (C-H) insertion into the alkyl group to give the 2-azetidinone and/or 2-pyrrolidinone derivatives was observed.The chemoselectivity of the rhodium carbenoid C-H insertion can be altered by the use of the α-acetyl and α-phenylsulfonyl substituents.In these cases, exclusive C-H insertion at the N-aryl moiety resulted to give 2(3H)-indolinone products.However, the α-substituent effect on the chemoselectivity of the insertion reaction is easily overridden by conformational effects about the amide N-C(O) bond as revealed by the insertion reaction of the conformationally rigid compounds 20a-c.The α-substituent effects are reestablished when conformational rigidity is removed, as exemplified by the rhodium carbenoid insertion reactions of compounds 29a, b.
Stereoselective Synthesis of β-Lactams by Oxidative Coupling of Dianions of Acyclic Tertiary Amides
Kawabata, Takeo,Minami, Tatsuya,Hiyama, Tamejiro
, p. 1864 - 1873 (2007/10/02)
Tertiary amides RCH2CON(R')CH2Z, where Z is an electron-withdrawing group, were converted into dianions by treatment with 2 equiv of n-butyllithium or tert-butyllithium, and the dianions were oxidized with N-iodoosuccinimide (NIS) or a Cu(II) carboxylate to form β-lactams stereoselectively.The stereochemistry of β-lactam formation depends on the oxidant; NIS is cis-selective, whereas Cu(II) is nonselective or slightly trans-selective.A high degree of asymmetric induction in the formation of β-lactams was achieved by using (R)-1-phenylethylamines a chiral auxiliary.This asymmetric ring closure was applied to the preparation of cis-β-lactam 31, an intermediate for the synthesis of the monobactam antibiotic carumonam.
STEREOSPECIFIC SYNTHESIS OF CHIRAL PRECURSORS OF THIENAMYCIN FROM L-THREONINE
Shiozaki, Masao,Ishida, Noboru,Hiraoka, Tetsuo,Maruyama, Hiroshi
, p. 1795 - 1802 (2007/10/02)
L-Threonine was transformed, stereospecifically, to a versatile β-lactam (5a) in 3 steps.This β-lactam was further converted to a key intermediate (25) for the synthesis of thienamycin and its biologically active analogues.Furthermore, the compound 5a was changed to iodides (18 and 23), cyanides (19 and 24), chloromethylketone (26) and aldehydes (30 and 31) which appear to have a latent potential as precursors for the syntheses of the carbapenems.
