Abstract
We demonstrate the borrowing hydrogen reaction of readily available 2-aminobenzyl alcohol 1, which is a new synthetic strategy for the construction of ring-fused quinazoline systems. The cascade reaction involves the dehydrogenative oxidation of alcohol 1 to the corresponding aldehyde 3 followed by self-condensation and reduction utilizing the benzyl Pd(II) system. The racemate 2 was successfully separated by chiral HPLC, affording a pair of enantiomers with high purity (>99 % ee) in a 1:1 ratio. The absolute configuration of one enantiomer was established via X-ray crystallography of its heavy atom analog. The structures of the racemate 2 and the pure enantiomer 2a were characterized by single-crystal X-ray analysis.
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