765313-44-8Relevant academic research and scientific papers
A novel and environmental friendly synthetic route for hydroxypyrrolidines using zeolites
Fan,Chuah,Jaenicke, Stephan
, p. 103 - 114 (2018/12/13)
A critical step in the synthesis of the hydroxypyrrolidines, 1,4-dideoxy-1,4-imino-L-lyxitol and 1,4-dideoxy-1,4-imino-D-lyxitol, from the corresponding D-sugars is the synthesis of O-methyl 2,3-O-isopropylidenepentofuranoses. Instead of applying homogeneous catalysis process with conventional inorganic acid catalysts like HCl and HClO4, it was found that heterogeneous catalysis using zeolites could be used for the one-pot synthesis of O-methyl 2,3-O-isopropylidenepentofuranoses directly from D-sugars, MeOH and acetone at mild condition. The best catalyst was H-beta zeolite containing a Si/Al molar ratio of 150, where a yield of >83% was obtained. The overall yields of the five-step procedure to 1,4-dideoxy-1,4-imino-L-lyxitol and 1,4-dideoxy-1,4-imino-D-lyxitol were 57% and 50%, respectively. This synthetic procedure has several advantages such as competitive overall yield, reduced number of steps, and mild reaction conditions. Furthermore, the zeolite catalyst can be easily recovered from the reaction mixture and reused with no loss of activity.
A fast, efficient and stereoselective synthesis of hydroxy-pyrrolidines
Dangerfield, Emma M.,Gulab, Shivali A.,Plunkett, Catherine H.,Timmer, Mattie S. M.,Stocker, Bridget L.
experimental part, p. 1360 - 1365 (2010/10/02)
A five-step, protecting group free synthesis of 2,3-cis substituted hydroxy-pyrrolidines is presented. Key steps in the synthesis are the chemoselective formation of a primary amine via a Vasella reductive amination using ammonia as the nitrogen source, and the stereoselective formation of a cyclic carbamate from an alkenylamine. Improvement of the reductive amination, by way of the use of α-picoline borane as a more environmentally benign reducing agent, is also presented.
The combined use of stereoelectronic control and ring closing metathesis for the synthesis of (-)-8-epi-swainsonine
Murray, Adrian J.,Parsons, Philip J.,Hitchcock, Peter
, p. 6485 - 6492 (2008/02/04)
A novel and efficient synthesis of (-)-8-epi-swainsonine 2 is reported. Stereocontrolled diol formation from the bicyclic alkene 3 followed by a stereoselective vinylation of the aldehyde and ring closing metathesis gave the indolizidine ring system, which was converted into (-)-8-epi-swainsonine 2.
A convenient approach to (-)-8-epi-swainsonine
Murray, Adrian J.,Parsons, Philip J.
, p. 1443 - 1445 (2007/10/03)
A novel and efficient synthesis of (-)-8-epi-swainsonine (2) is reported. Face-selective diol formation from the bicyclic alkene 3 followed by a stereoselective vinylation of the aldehyde and ring-closing metathesis gave the indolizidine ring system, which was converted into (-)-8-epi-swainsonine (2). Georg Thieme Verlag Stuttgart.
Novel routes to the kainates: Stereoselectivity in addition reactions to pyrrole [1,2c]-oxazol-3-one
Murray,Parsons,Greenwood,Viseux
, p. 1589 - 1591 (2007/10/03)
This paper describes the addition of a range of electrophiles to 1. An unusual and unpredicted stereochemistry of addition has been observed in line with our original photochemical observations.
