In unravelling the mechanism of the reaction, chemists protected the nitrogen atom with Iloc
(Chapter 25) before the reaction y,}ith benzaldehyde and found that a new product was formed that was clearly an E-alkene as its NMR spectrum contained SH 6.73 (1H, d, ] 16). This is too large a coupling constant even for axiallaxial protons and can be only trr}ns coupling across a double bond.
They quickly deduced that a simple aldol reaction had happened.
When the Boc protecting group was removed, the cyclization reaction occurred under very mild conditions but now a single diastercoisamer of the product was formed.
This isomer had one proton that could be clearly seen at $H 4.27 p.p.m.-well away from all the
rest. This is the proton marked in black between nitrogen and the phenyl group. It was a double dou-
blet with]=6 and 4 flz. Neither of these is large enough to be an axiallaxial coupling but h Hz is
within the range for axiallequatorial and 4 Hz for equatoriallequatorial coupling. The compom记
must have the conformation shown in the margin.
Treatment of this product with stronger base (NaOH) isomerized it to a compound in which