Abstract
The 7-endo-trig and 6-exo-trig cyclizations of the N-formylphenethylenamide radicals have been computationally studied at the UM062X/6–31 + G** and UPW6B95-D3 DFT levels of theory. Computations show a regioselectivity preference for the 7-endo process over the 6-exo in agreement with known experimental results. This 7-endo process takes place preferentially through a transition structure of half-boat geometry which fully retains enamide planarity. On the other hand, the 6-exo-trig cyclization prefers a chair transition structure geometry which places the N-vinyl group in a pseudo-equatorial position. Computations also show that conformational locking in cyclic enamides greatly increases the preference for the 7-endo path in agreement with experimentally observed outcomes.
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