Synthesis of dienyl ketones via palladium(II)-catalyzed direct cross-coupling reactions between simple alkenes and vinyl ketones: application to the synthesis of vitamin A1 and bornelone

Xiang Zhang; Min Wang; Ming-Xin Zhang; Yun-He Xu; Teck-Peng Loh

doi:10.1021/ol402692t

Synthesis of dienyl ketones via palladium(II)-catalyzed direct cross-coupling reactions between simple alkenes and vinyl ketones: application to the synthesis of vitamin A1 and bornelone

Org Lett. 2013 Nov 1;15(21):5531-3. doi: 10.1021/ol402692t. Epub 2013 Oct 16.

Authors

Xiang Zhang¹, Min Wang, Ming-Xin Zhang, Yun-He Xu, Teck-Peng Loh

Affiliation

¹ Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China , 96 Jinzhai Road, Hefei, Anhui 230026, China, and Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University , 637371, Singapore.

PMID: 24131401
DOI: 10.1021/ol402692t

Abstract

An efficient and general method for the synthesis of conjugated dienyl ketones via palladium(II) acetate catalyzed direct cross-coupling between simple alkenes and vinyl ketones is reported. This method has been successfully applied for the synthesis of Vitamin A1 and bornelone.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkenes / chemical synthesis*
Alkenes / chemistry
Camphanes / chemical synthesis*
Camphanes / chemistry
Catalysis
Ketones / chemical synthesis*
Ketones / chemistry
Molecular Structure
Palladium / chemistry*
Vinyl Compounds / chemical synthesis*
Vinyl Compounds / chemistry
Vitamin A / chemical synthesis*
Vitamin A / chemistry

Substances

Alkenes
Camphanes
Ketones
Vinyl Compounds
Vitamin A
Palladium
bornelone