7218-27-1Relevant academic research and scientific papers
A "traceless" Directing Group Enables Catalytic SN2 Glycosylation toward 1,2- cis-Glycopyranosides
Fu, Yue,Liu, Peng,Ma, Xu,Zhang, Liming,Zheng, Zhitong,Zhu, Xijun
supporting information, p. 11908 - 11913 (2021/08/20)
Generally applicable and stereoselective formation of 1,2-cis-glycopyranosidic linkage remains a long sought after yet unmet goal in carbohydrate chemistry. This work advances a strategy to this challenge via stereoinversion at the anomeric position of 1,2-trans glycosyl ester donors. This SN2 glycosylation is enabled under gold catalysis by an oxazole-based directing group optimally tethered to a leaving group and achieved under mild catalytic conditions, in mostly excellent yields, and with good to outstanding selectivities. The strategy is also applied to the synthesis of oligosaccharides.
Inhibitory effects of N-(acryloyl)benzamide derivatives on tyrosinase and melanogenesis
Lee, Sanggwon,Ullah, Sultan,Park, Chaeun,Won Lee, Hee,Kang, Dongwan,Yang, Jungho,Akter,Park,Chun, Pusoon,Moon, Hyung Ryong
, p. 3929 - 3937 (2019/07/30)
Targeting of tyrosinase has proven to be the best means of identifying safe, efficacious, and potent tyrosinase inhibitors for whitening skin. We designed and synthesized ten NAB (N-(acryloyl)benzamide) derivatives (1a–1j) using the Horner-Wadsworth-Emmon
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.
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
Catalytic Asymmetric Total Syntheses of Quinine and Quinidine
Raheem, Izzat T.,Goodman, Steven N.,Jacobsen, Eric N.
, p. 706 - 707 (2007/10/03)
The catalytic, asymmetric syntheses of quinine and quinidine were achieved in 16 steps. The recently developed salen(Al)-catalyzed enantioselective Michael addition of methyl cyanoacetate served to set the crucial C4 stereocenter in 92% ee, and a late-stage asymmetric dihydroxylation was used to differentiate the common intermediate and access the two desired diastereomeric products with high selectivity. Copyright
A Practical Synthesis of α,β-Unsaturated Imides, Useful Substrates for Asymmetric Conjugate Addition Reactions
Goodman, Steven N.,Jacobsen, Eric N.
, p. 953 - 956 (2007/10/03)
We report an improved synthesis of α,β-unsaturated imides, a class of compounds that has been identified as broadly useful in (salen)aluminum-catalyzed asymmetric conjugate addition reactions. An efficient, scaleable procedure for the synthesis of phospho
