What is the significance of the hydrated scandium triflate in achieving high diastereoselectivity?

Label:chem

Topic
A study explores the use of hydrated scandium triflate as a Lewis acid catalyst in the diastereoselective allylation of (S)-3-(methoxymethyl)hexanal. The hydration of the catalyst is found to be crucial for achieving high diastereoselectivity.
Answer
The hydrated form of scandium triflate (Sc(OTf)₃) is essential for achieving high diastereoselectivity in the allylation reaction. The addition of water to the anhydrous catalyst improves its performance by introducing additional steric hindrances, which further enhance the difference in reactivity between the chelate intermediates. This leads to a higher yield and better diastereoselectivity (up to 94:6) compared to using the anhydrous form of the catalyst.
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