What is the role of scandium triflate in the diastereoselective allylation of (S)-3-(methoxymethyl)hexanal?

Label:chem

Topic
A study explores the use of scandium triflate as a Lewis acid catalyst in the diastereoselective allylation of (S)-3-(methoxymethyl)hexanal with β-(2,2-diethoxyethyl)-substituted (allyl)tributylstannane. The goal is to achieve high 1,3-anti-diastereoselectivity in the synthesis of (+)-Neopeltolide.
Answer
Scandium triflate (Sc(OTf)₃) plays a crucial role as a Lewis acid catalyst in the diastereoselective allylation of (S)-3-(methoxymethyl)hexanal. The hydrated form of scandium triflate was found to be essential for achieving high 1,3-anti-diastereoselectivity (d.r. 94:6), while the anhydrous form resulted in lower diastereoselectivity (d.r. 76:24). The addition of water to the anhydrous catalyst improved its performance, leading to better diastereoselectivity and yield.
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