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. Author manuscript; available in PMC: 2013 Jan 1.
Published in final edited form as: Int J Quantum Chem. 2012 Jan 1;112(2):509–518. doi: 10.1002/qua.23020

Figure 6.

Figure 6

Optimized TS structures for Additions onto Imine 5 using Sulfur Ylide 1. Structures and energies determined at the B3LYP/6-311+G**(THF) level of theory; energies are ZPE-corrected and relative to reactants. Significant interaction distances are indicated. Top: The R configuration of the sulfinyl sulfur permits ylide approach to the Re face; Re face approach is favored in spite of a steric clash with BDA. Bottom: The sulfinyl oxygen/iminyl hydrogen interaction is disrupted to permit Si approach, but Si approach occurs without steric clash with BDA. Imine 5's N- and S- substituents are not matched, with the former favoring Re addition and dominant, while the latter favors Si addition.