A Mild Protocol for Allylation and Highly Diastereoselective Syn or Anti Crotylation of Aldehydes in Biphasic and Aqueous Media Utilizing Potassium Allyl- and Crotyltrifluoroborates

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Abstract
Potassium allyl- and crotyltrifluoroborates undergo addition to aldehydes in biphasic media as well as water to provide the corresponding homoallylic alcohols in high yields (≥94%), excellent diastereoselectivity (dr ≥ 98:2), and without the necessity of any subsequent purification. The presence of a phase transfer catalyst (e.g., nBu4NI) significantly accelerates the rate of reaction, whereas added fluoride ion retards the reaction.