Previously unknown tributyl-[(2-methylidene-4,4-diethoxy)butyl]stannane was prepared from diethyl acetal of 3-(bromomethyl)but-3-enal and was brought subsequently into a catalytic asymmetric Keck allylation of butanal in order to obtain optically active homoallylic alcohol. The use of activating additives [B(OBu)3 and CF3COOH] favors the process proceeding with high yields and enantioselectivity. An approach was suggested to the synthesis of С14–С21 fragments of amphidinolide Т applying tributyl[(2-methylidene-4,4-diethoxy)butyl]stannane in the key stage of building up the carbon scaffold.

Tributyl-[(2-methylidene-4,4-diethoxy)butyl]stannane can be used for asymmetric allylation of butanal to obtain optically active homoallylic alcohol, potentially aiding in the synthesis of 14-21 fragments of am

Paper

Synthesis of β-(2,2-diethoxyethyl)-substituted (allyl)tributylstannane and its application to asymmetric allylation

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