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. Author manuscript; available in PMC: 2013 Apr 18.
Published in final edited form as: J Am Chem Soc. 2012 Apr 10;134(15):6528–6531. doi: 10.1021/ja300369c

Figure 1.

Figure 1

Pathways for 1,3-allylic rearrangement/Schmidt reactions of (a) 1c and 1d (or substituted cyclohexanones bearing an equatorial side chain, like 7a) and (b) 9c and 9d. In (a), the numbers in parentheses indicate calculated energies for transition state structures from the indicated intermediate to the corresponding LA-complexed lactam product (CPCM(DCM)-B3LYP/6-31G(d,p)[SDD for Sn], relative to the lowest energy transition state structure). (c) Disfavored intermediates from isomers of 11. Proposed intermediates from (d) isomers of 13 or (e) isomers of 19.