Direct synthesis of conjugated tetraenes from 1,3-enynes with 1,3-dienes

被引：1

作者：

Maekawa, Kanako ^{[1
]}

Komine, Nobuyuki ^{[1
]}

Kiyota, Sayori ^{[1
]}

Hirano, Masafumi ^{[1
]}

机构：

[1] Tokyo Univ Agr & Technol, Grad Sch Technol, Dept Appl Chem, 2-24-16 Nakacho, Koganei, Tokyo 1848588, Japan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2024年 / 22卷 / 10期

关键词：

PALLADIUM-CATALYZED ALKOXYCARBONYLATION; STEREOSELECTIVE-SYNTHESIS; TRANSFER HYDROGENATION; POLYENE;

D O I：

10.1039/d4ob00077c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New direct access to conjugated tetraenes has been achieved. A Ru(0)-catalysed reaction of 1,3-enynes with 1,3-dienes gives 1,3,5,7-octatetraene derivatives by formal regioselective insertion of the alkynyl group of 1,3-enynes into the terminal C-H bond in 1,3-dienes. With a silyl substituent on the alkynyl side in 1,3-enynes, the reaction regioselectively proceeds to give the linear cross-dimerisation product having the silyl group at the internal position. Stoichiometric and DFT calculations support the oxidative coupling mechanism for the linear cross-dimerisation. Methyl (2E,4E,6E,8E)-10-hydroxy-2,4,6,8-decatetraenoate, a versatile polyene intermediate, is accessed by this method as a formal synthesis of biologically active compounds. New direct access to conjugated tetraenes has been achieved by cross-dimerisation of 1,3-enynes with 1,3-dienes.

引用

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页码：2098 / 2114

页数：17

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