Abstract
Aza-Diels−Alder reaction between 2-[(R)-1-phenylethyl]iminoethanoate (1) and cyclopentadiene using the biphasic solvent system (TMSCl−CH3OH/toluene) gave (1S,3S,4R)-2-[(R)-1-phenylethyl]-2-aza-bicyclo[2.2.1]hept-5-ene-3-carboxylates (3a) in 32% isolated yield. The present method is advantageous for the large-scale synthesis, because (i) the reported methods required harmful and expensive fluorinated chemicals, (ii) methyl analogue 3a was practically isolated as a crystalline solid, and (iii) the reaction was conducted with very little observable exotherm. In addition, the absolute configurations of the other three diastereomers 2, 4, and 5 were unambiguously determined.
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