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Highly stereoselective synthesis of 6-perfluoroalkyl-6-fluoroalka-2,3,5-(Z)-trienols through carbometallation-elimination of 5-perfluoroalkyl-substituted 4(E)-alken-2-ynols with Grignard reagents

✍ Scribed by Zhichao Ma; Rong Zeng; Yihua Yu; Shengming Ma

Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
376 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis

A highly regio-and stereoselective sequential carbometallation and Z-selective b-elimination reaction of 5-perfluoroalkyl-4(E)-en-2-ynols with Grignard reagents in Et 2 O has been developed to afford various 6perfluoroalkyl-6-fluoroalka-2,3,5(Z)-trienols in good to excellent yields. Primary or secondary alkyl or aryl Grignard reagents may be used to introduce the R 2 group to the 2-position of the starting materials referring to the hydroxyl group. A mechanism for this transformation has been proposed.

📜 SIMILAR VOLUMES

ChemInform Abstract: Highly Stereoselect
ChemInform Abstract: Highly Stereoselective Synthesis of 6-Perfluoroalkyl-6-fluoroalka-2,3,5-(Z)-trienols Through Carbometallation—Elimination of 5-Perfluoroalkyl-Substituted 4(E)-Alken-2-ynols with Grignard Reagents.
✍ Zhichao Ma; Rong Zeng; Yihua Yu; Shengming Ma 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 31 KB

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