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. Author manuscript; available in PMC: 2013 Aug 17.
Published in final edited form as: J Org Chem. 2012 Jun 6;77(16):6689–6702. doi: 10.1021/jo300635m

Figure 2.

Figure 2

Mechanistic Rationale for the Observed Diastereoselectivity. A/The experimental data supports the thermodynamic control of the stereoselectivity. The stereoisomer with the α-aryl group in the axial position is more stable due to the steric bulk of the N-tosyl group and its position on a partially sp2-hybridized nitrogen. ORTEP diagram from the X-ray analysis of the major isomer 11 is shown (right side). B/ The same ratinonale explains the formation of the cis-isomer of 2,5-disubstituted piperidine 19 as the major product. ORTEP diagram of 19 is shown (right side).