Stereocomplementary Syntheses of 1,ω‐Distannylated  E , Z ‐Isomeric Conjugated Trienes, Tetraenes, and Pentaenes | Zendy

Burghart Jochen | Zendy; Sorg Achim | Zendy; Brückner Reinhard | Zendy

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

Author(s) -

Burghart Jochen,

Sorg Achim,

Brückner Reinhard

Publication year - 2011

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201001629

Subject(s) - hexa , chemistry , stereoselectivity , conjugated system , medicinal chemistry , stereochemistry , double bond , organic chemistry , catalysis , polymer

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 CC 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 Bu 3 Sn‐substituted enals or dienals with Bu 3 Sn‐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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