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36.1.7.3.5 Variation 5: Lewis Acid Catalyzed Addition of Allylic Silane and Stannane Reagents

DOI: 10.1055/sos-SD-036-00193

Frost, C. G.; Le Nôtre, J.Science of Synthesis, (200836326.

The addition of allylsilanes and allylstannanes to aldehydes has been extensively studied as a mild and efficient method for the synthesis of alcohols.[‌346‌] The reactions are promoted by Lewis acids, Lewis bases, or additionally by fluoride ion in the case of allylsilanes. Interestingly, the Lewis acid promoted addition of but-2-enylsilanes provides predominantly syn-homoallyl alcohol 118A no matter what the geometry of the double bond in the starting material (Scheme 66).[‌351‌] Similarly, the Lewis acid induced syn addition of allylstannanes to alkyl aldehydes is independent of initial allyl geometry.[‌352‌]

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