Esterification ring opening with

Epoxidation of the simplest allylic alcohol, allyl alcohol 7, is achieved in 88-92% ee with yields of 50-60% using diisopropyl tartrate as ligand. In situ derivatization of the product glycidol 8 via esterification, sulfonylation, or ring opening with nucleophile is an attractive alternative to isolating glycidol. 

Dioxepanes 63 were hydrolyzed with aqueous hydrochloric acid to the starting diol. A thionyl chloride promoted ring-opening of dioxepane 63 to intermediate 64 has been reported. When treated with base, compound 64 can be transformed into vinylic ether 65 in 58% yield (81ZOR1047) (Scheme 31). 3-Methylfurazan-4-acetic acid was converted to the vinyl derivative 66 via an esterification, reduction, mesylation, and base elimination sequence (81JHC1247) (Scheme 31). 

As compared to the esterification of sucrose, cataly tic etherification of sucrose provides another family of non-ionic surfactants that are much more robust than sucrose esters in the presence of water. Synthesis of sucroethers can be achieved according to two processes (1) the ring opening of epoxide in the presence of a basic catalyst and (2) the telomerization of butadiene with sucrose using a palladium-phosphine catalyst. 

Lipase Transesterification and direct esterification (inch polyester synthesis) Ring-opening polymerization of 8-caprolactone Hydrolysis alcoholysis acetylation Higher stability of enzyme greater activity catalyst recyclable sometimes higher enantio- and regio-selectivity compared with VOCs... 

Substituted oxazolidin-5-one derivatives, which are prepared from N -protected a-annino dicarboxyhc acids and paraformaldehyde, are employed for dual protection of the a-annino and a-carboxy groups in the synthesis of P-aspartyl and y-glutamyl esters (Scheme 4).Py For this purpose the oxazolidinone derivatives are synthesized by treatment of the Z amino acids with paraformaldehyde in a nnixture of acetic anhydride, acetic acid, and traces of thionyl chloride or by azeotropic distillation of the Z amino acids with paraformaldehyde and 4-toluenesulfonic acid in benzene. The resulting heterocychc compounds are readily converted into the tert-butyl esters with isobutene under acid catalysis. Esterification is achieved with tert-butyl bromidet or with Boc-F.P l Finally, the oxazolidinone ring is opened by alkaline hydrolysis or catalytic hydrogenolysis to yield the tert-butyl esters. 

Starting from ethyl 4, 4, 4-trifluorocrotonate, racemic aziridine carboxylic acid 96 was prepared as shown in Scheme 9.22 [46] and was then subjected to lipase-catalyzed esterification. Methyl ester 97 was obtained in 35% yield with excellent enantiomeric purity. Acid-catalyzed ring opening of aziridine 97 proceeded regio- and stereoselectively, affording 2-substituted (2R,3R) or (2/ ,3S)-3-amino-4,4,4-trifluorobutanoates 98 in high yields [47]. 

The vitality of this field is further demonstrated by a continuous search for original ways of exploiting vegetable oils. Examples include self-healing elastomers in which fatty acids play a central role [46] the esterification of cellulose with fatty acids to give thermoplastic materials [47] the synthesis of a saturated aliphatic diisocyanate from oleic acid and its subsequent use in the preparation of fully biobased polyurethanes in conjunction with canola oil-derived polyols [48] and novel elastomers from the concurrent cationic and ring-opening metathesis polymerization of a modified linseed oil [49]. 

Hb = H, which underwent Curtius rearrangement with retention of configuration at the labeled carbon followed by deprotection to give the labeled samples of isoserine 85. Esterification, N tritylation, O tosylation, and ring closure then led to the labeled aziridines 86 which underwent ring opening and deprotection in perchloric acid to yield 2R, 3R)-[2,3- H2]- and 2R, 3S)-[3- H,]serines 60f, Ha = H, and 60f, Hb = H, respectively (94). 

Concomitant ring opening of lactone 275 and esterification of the resulting a-hydroxy acid with trimethylsilyl iodide in ethanol produces iodoester 296. Subsequent treatment with propargylamine affords pyrrolidinone 297 in 45% overall yield from ( S)-malic acid. The product is used as an intermediate for the preparation of hydroxyl-containing oxotremorine analogs potentially useful for the treatment of senile dementia [40]. 

An alternative to the experiments just described is the esterification of chitosan with the use of lactide or polylactide for example, Skotak et al. [59] prepared chitosan derivatives following a one pot approach by grafting L-lactide oligomers via ring-opening polymerization. Chitosan (600 mg) was dissolved in 10 mL of... 

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