Transition Metal‐Assisted Transformations of Diversely Functionalized Dienynes | Zendy

MarcoContelles José | Zendy; Mainetti Emily | Zendy; Fensterbank Louis | Zendy; Malacria Max | Zendy

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Transition Metal‐Assisted Transformations of Diversely Functionalized Dienynes

Author(s) -

MarcoContelles José,

Mainetti Emily,

Fensterbank Louis,

Malacria Max

Publication year - 2003

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200310007

Subject(s) - chemistry , stannane , cycloisomerization , stereocenter , yield (engineering) , stereoselectivity , adduct , trimethylsilyl , catalysis , palladium , organic chemistry , medicinal chemistry , transition metal , enantioselective synthesis , materials science , metallurgy

We report the triphenyltin‐mediated free‐radical cyclization of 4‐ethynyl‐2,6,6‐trimethylocta‐1,7‐dien‐4‐ol ( 1 ) and 4‐ethynyl‐6,6‐dimethylocta‐1,7‐dien‐4‐ol ( 2 ), along with some chemical manipulations of the resulting stannylidene derivatives 3 and 7 . The reaction of intermediates 3 and 7 with BuLi afforded the protodestannylated compounds 5 and 8 , respectively, in good yield, while the reaction of the mixture of adducts 3 and 4 with iodine gave the chloro(diphenyl)stannylidene derivatives 6 and 6′ . The palladium dichloride catalyzed reaction of dienyne 1 with tributyl(trimethylsilyl)stannane has also been described. All these cycloisomerization reactions were highly stereoselective, affording unique isomers at the newly formed stereocenters. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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