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Stereocomplementary Syntheses of 1,ω-Distannylated E,Z-Isomeric Conjugated Trienes, Tetraenes, and Pentaenes

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Abstract

Stereoselective syntheses of 1,6-bis(tributylstannyl)hexa-1,3,5-trienes, 1,8-bis(tributylstannyl)octa-1,3,5,7-tetraenes, and 1,10-bis(tributylstannyl)deca-1,3,5,7,9-pentaenes with various methylation patterns were achieved based on stereocomplementary C[DOUBLE BOND]C bond-forming reactions. All-E isomers resulted from Ramberg–Bäcklund rearrangements of distannylated diallyl-, allylpentadienyl-, or bis- (pentadienyl)sulfones. Mono-Z-configured 1,ω-bis(tributylstannyl)-1,3,5-polyenes emerged from (Sylvestre–)Julia olefinations of Bu3Sn-substituted enals or dienals with Bu3Sn-substituted allyl or pentadienyl benzothiazolylsulfones. Related Ramberg–Bäcklund approaches provided all-E-1-bromo-6-(tributylstannyl)hexa-1,3,5-triene but not all-E-1-(tetramethyldioxaborolanyl)-6-(tributylstannyl)hexa-1,3,5-triene.

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