80542-16-1Relevant articles and documents
Pd-catalyzed intramolecular aminohydroxylation of alkenes with hydrogen peroxide as oxidant and water as nucleophile
Zhu, Haitao,Chen, Pinhong,Liu, Guosheng
, p. 1766 - 1769 (2014/03/21)
A palladium-catalyzed intramolecular aminohydroxylation of alkenes was developed, in which H2O2 was applied as the sole oxidant. A variety of related alkyl alcohols could be successfully obtained with good yields and excellent diastereoselectivities, which directly derived from oxidation cleavage of alkyl C-Pd bond by H2O2. Facile transformation of these products provided a powerful tool toward the synthesis of 2-amino-1,3-diols and 3-ol amino acids. Preliminary mechanistic studies revealed that major nucleophilic attack of water (SN2 type) at high-valent Pd center contributes to the final C-O(H) bond formation.
Direct-type aldol reactions of fluorenylidene-protected/activated glycine esters with aldehydes for the synthesis of β-hydroxy-α-amino acid derivatives
Rahmani, Raphael,Matsumoto, Masatoshi,Yamashita, Yasuhiro,Kobayashi, Shu
, p. 1191 - 1194 (2012/07/28)
Two birds with one stone: Magnesium-base-catalyzed highly diastereoselective direct-type aldol reaction of glycine Schiff base bearing a fluorenylidene moiety as a protecting and activating group was developed. The desired reactions proceeded smoothly at low temperature, and the aldol products were obtained in high yield with high diastereoselectivity. Copyright
Spirodiketopiperazine-based CCR5 antagonist: Discovery of an antiretroviral drug candidate
Nishizawa, Rena,Nishiyama, Toshihiko,Hisaichi, Katsuya,Minamoto, Chiaki,Matsunaga, Naoki,Takaoka, Yoshikazu,Nakai, Hisao,Jenkinson, Stephen,Kazmierski, Wieslaw M.,Tada, Hideaki,Sagawa, Kenji,Shibayama, Shiro,Fukushima, Daikichi,Maeda, Kenji,Mitsuya, Hiroaki
, p. 1141 - 1145 (2011/04/16)
Following the discovery that hydroxylated derivative 3 (Fig. 1) was one of the oxidative metabolites of the original lead 1, it was found that hydroxylated compound 4 possesses higher in vitro anti-HIV potency than the corresponding non-hydroxylated compo
ENANTIOSPECIFIC AND DIASTEREOSELECTIVE SYNTHESIS OF ANTI α-HYDRAZINO- AND α-AMINO-β-HYDROXYACIDS THROUGH "ELECTROPHILIC AMINATION" OF β-HYDROXYESTERS
Guanti, Giuseppe,Banfi, Luca,Narisano, Enrica
, p. 5553 - 5562 (2007/10/02)
β-Hydroxyesters 1a-d were transformed into corresponding dianions and condensed with di-t-butylazodicarboxylate to give anti protected α-hydrazino-β-hydroxyesters 2a-d with good diastereoselectivities (up to 94:6).Cleavage of protecting groups followed by ester hydrolysis gave the previously unknown anti α-hydrazino-β-hydroxyacids 4a-d, which were in turn converted by hydrogenolysis into anti α-amino-β-hydroxyacids 5a-d.Starting from (S) 1a, enantiomerically pure (2S,3S) allo-threonine 5a was obtained in good overall yields.On the contrary, reaction of silyl ketene acetal 10, derived from 1a, with a diazonium salt furnished predominantly the syn isomer, but in unsatisfactory yield.
