Beilstein J. Org. Chem.2006,2, No. 19, doi:10.1186/1860-5397-2-19
obtained after a dehydrobromination reaction. The elimination of hydrogen bromide from such β-fluorobromides had been explored previously, and the reaction proceeds in a stereospecific manner to generate either E or Z fluoroalkene products [20]. Accordingly treatment of 14 with potassiumtert-butoxide in a
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Graphical Abstract
Scheme 1:
Synthesis of vicinal dimethyl difluorosuccinates. The conversion of the tartrates 1 with SF4 and HF ...
Beilstein J. Org. Chem.2005,1, No. 7, doi:10.1186/1860-5397-1-7
deprotection of the TBS ether by using 3HFEt3N afforded mesylates 11 (80 – ≥ 95% yield). Treatment of mesylate 11a with 1 equivalent of potassiumtert-butoxide in tert-BuOH (0.01 M) between 40–50 °C provided ent-3a in 75% yield and 10:1 selectivity for the dihydropyran product and a diene resulting from an