19377-75-4Relevant articles and documents
Formation of five-membered carbocycles from D-glucose: A Concise Synthesis of 4-Hydroxy-2-(hydroxymethyl)cyclopentenone
Koseki, Yoshitaka,Watanabe, Toshihiro,Kamishima, Takaaki,Kwon, Eunsang,Kasai, Hitoshi
, p. 1324 - 1328 (2019/09/18)
A concise synthesis of 4-hydroxy-2-(hydroxymethyl)cyclo-pentenone (1) has been accomplished from D-glucose by a three-step sequence that features a catalyst-free hydrothermal reaction of D-glucal, which is readily obtained from D-glucose. Optimization of the reaction conditions for synthesizing 1 was performed by changing the temperature and reaction time. The treatment of D-glucal under the optimal conditions, i.e., at 120 °C for 24 h, provided 1 in the highest isolated yield of 61%. 1 would become a versatile intermediate for the synthesis of various fine chemicals having a cyclopentenone structure from cellulosic biomass.
Synthesis of chiral unsaturated aminolactones using Pd-catalyzed allylic amination
Kallinen, Annukka,Tois, Jan,Sjoeholm, Rainer,Franzen, Robert
experimental part, p. 2367 - 2371 (2010/12/25)
Stereoselective synthesis of (5R,6R)- and (5S,6S)-5-benzylamino-6-(tert- butyldimethylsilanyloxymethyl)-5,6-dihydropyran-2-ones starting from d-glucal and furanaldehyde, respectively, is described. The synthesis relies on a Sharpless asymmetric dihydroxylation, an Achmatowicz reaction, and a stereoselective Pd-catalyzed allylic amination as the key steps.
Synthesis of enantiopure chloroalcohols by enzymatic kinetic resolution
Haak, Robert M.,Tarabiono, Chiara,Janssen, Dick B.,Minnaard, Adriaan J.,De Vries, Johannes G.,Feringa, Ben L.
, p. 318 - 323 (2008/03/27)
3-Alkenyl and heteroaryl chloroalcohols have been obtained in excellent enantiomeric excess (>99%) by enzymatic kinetic resolution using the haloalcohol dehalogenase HheC. Yields were close to the theoretical maximum for all substrates employed. Furthermo
