Anomeric effect implications

A. J. Weldon, T. L. Vickrey, and G. S. Tschumper, Intrinsic conformational preferences of substituted cyclohexanes and tetrahydropyrans evaluated at the CCSD(T) complete basis set limit Implications for the anomeric effect, J. Phys. Chem. A, 109 (2005) 11073—11079. 

Mikolajczyk, M.. Graczyk, P. and Wieczorek, M.W., Conformational preference in L3-dithianes containing 2-phosphoryl. -(thiophosphoryl), and -(selenophosphoryl) groups. Chemical and crystallographic implications of the nature of the anomeric effect, J. Org. Chem., 59. 1672, 1994. 

We have learnt above enough about the anomeric effect and its implications on conformational preferences. Let us take a look at the examples from the general literature given in Eqs. 42-45 and analyze them in the manner as above. The... 

Anomeric Effect and Electron Density Spectroscopic Implications of Anomeric Effect... 

Molecular Mechanics- and Molecular Orbital-derived Implications of Anomeric Effect in Y—C—P System (Y = O, S, Se)... 

The nature of the anomeric effect operative in the S—C—P system will be considered taking into account (1) thermodynamic, (2) MM- and MO-based, (3) X-ray crystallographic, (4) spectroscopic, and (5) kinetic implications. It must be added that solvent studies were shown to be not useful to reveal... 

Kinetic Implications of Anomeric Effect in S—C—P System These were discussed in Section IV.A.l. 

Chelation control has also been implicated in conjugate addition reactions. For example, during a synthesis of the macrolide antibiotic 6-ep/-erythromycin, Mul-zer and co-workers86 found that the stereochemistry at the anomeric centre (l position) of the tetrahydropyranyl protecting group had a profound effect on the stereochemistry of conjugate addition of lithium dimethylcuprate to the ynone 49.1 [Scheme 1.49]. 

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