Oxazoline method

The oxazoline method is one of the excellent glycosylations for high stereoselectivity, in which the stereospecific glycosylation of alcohol with... 

Wolfe, J. P. Meyers Oxazoline Method In Name Reactions in Heterocycl. Chemistry, Li, J. J. Corey, E. J., Eds. Wiley Sons Hoboken, NJ, 2005, 237—248. (Review). 

In 1975 Meyers and coworkers, having studied reactions of Uthiated chiral oxazolines with various electrophiles, applied the chiral oxazoline method to conjugate addition of... 

Although the oxazoline method is a general procedure for the synthesis of 8-glycosides, the acylamido groups at C-2 of the starting materials are unchangeable to others. We next examined a more flexible method by which a variety of fatty acyl residues can be introduced after the formation of disaccharides (Figures 10 and 11). 

Micheel, F, Kochling, H, DarsteUung von glykosiden des D-glucosamins mit aliphatischen und aromatischen alkoholen und mit serin nach der oxazolin-methode, Chem. Ber., 91, 673-676, 1958. 

ProMem 26.16 Using the Meyers oxazoline method, outline all steps in the synthesis of (a) /i-butync acid from acetic acid (b) isobutyric acid from acetic acid (c) isobutyric acid from propionic acid (d) /3-phenylpropionic acid from acetic acid. 

This knowledge led to the development of the orthoester and oxazoline methods for producing 1,2-trans glycosides. 

In the oxazoline method, an oxazoline is treated with an alcohol in the presence of p-toluenesulfonic acid at 80 °C to produce a 2-acetamido-2-deoxyglycoside.61... 

This so-called oxazoline method was also applied for the synthesis of several crowded biaryls, [17] tetrasubstituted biphenyls [18], and binaphthyls [19], as well as the highly functionalized cyclic biphenyl moiety of vancomycin [20]. 

An alternative to the Meyers or Cram oxazoline methods is the use of 2-menthoxybenzoates for the synthesis of axially chiral biaryls. Treatment of the ester 34 with Grignard reagent 35 provides the (M)-biphenyl 36 in 94% e.e (ref. 23). However, poor enantioselectivities were observed in cases where an ortho chelating substituent on the Grignard reagent was absent. 

This synthetic application of 4,5-dihydrooxazoles is known as the Meyers oxazoline method [76]. 

Madelung synthesis (indole) 137 Marckwald cleavage, of furans 79 Marckwald synthesis (imidazole) 224 Meth-Cohn synthesis (quinoline) 402 Meyer s oxazoline method 183 Morin reaction 456 Mukaiyama reaction 380 Mukaiyama reagents 53, 380... 

In the field of 2-aniino-2-deoxY-D-glucose disaccharides the sugar in various derivatised forms has been linked to D-galactose (/9-1,3-link)(and /9-1,6-link),D-glucose (iS-l,3-link), 2-amino-2-deoxy-D-glucose (j8-l,4-link) D-galacturonic acid fi-1,2-link)and L-iduronic acid (a-l,4-link).The 2-amino-2,4-dideoxy-4-fluoro compound (55) has been prepared by the oxazoline method and 2-amino-2-deoxy- -D-mannopyranosyl disaccharides have been produced from oximo-products obtained by use of a 2-deoxy-2-oximo-D-arabino-hexosyl bromide. A 4-amino-4-deoxy-D-rhamnosyl disaccharide (a-l,2-linked) has been made by way of 4-azido-corapounds. 

A comparison of methods to generate azomethine ylides via 4-oxazohne ring opening vs. aziridine thermolysis has shown that the oxazoline method can produce the same azomethine dipole under kinetic control as the aziridine method under thermodynamic... 

The oxazoline method and two modifications of the H-phosphonate method have been used to obtain glycosyl phosphatidylinositol derivatives. ... 

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