"The stereochemical course of reactions at three-, four-, and five-member rings can be reliably predicted by assuming the relative congestion of the two faces. As the ring size increases above six so does the conformational mobility and hence the uncertainty of the stereochemical outcome. Even with seven-member rings, predictions are generally difficult."
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George S. Zweifel and Michael H. Nantz Modern Organic Synthesis (2006), Ch. 2. Stereochemical Considerations in Planning Syntheses
https://en.wikiquote.org/wiki/Stereochemistry
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Stereochemistry
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