The reactivity of epoxides with lithium 2, 2, 6, 6-tetramethylpiperidide in combination with organolithiums or Grignard reagents

DM Hodgson, MJ Fleming…

Index: Hodgson, David M.; Fleming, Matthew J.; Stanway, Steven J. Journal of Organic Chemistry, 2007 , vol. 72, # 13 p. 4763 - 4773

Full Text: HTML

Citation Number: 28

Abstract

The scope and limitations of lithium 2, 2, 6, 6-tetramethylpiperidide (LTMP)-modified reductive alkylation of epoxides is detailed. A variety of organolithiums are added to terminal and 2, 2-disubstituted epoxides in the presence of LTMP to generate alkenes in a completely regio-and highly stereoselective manner. Arylated alkenes, dienes, allylsilanes, and enynes are accessed using this procedure. The methodology is applied in the ...

Related Articles:

Alkenes from terminal epoxides using lithium 2, 2, 6, 6-tetramethylpiperidide and organolithiums or grignard reagents

[Hodgson, David M.; Fleming, Matthew J.; Stanway, Steven J. Journal of the American Chemical Society, 2004 , vol. 126, # 39 p. 12250 - 12251]

Ligand Effects on Negishi Couplings of Alkenyl Halides

[Krasovskiy, Arkady; Lipshutz, Bruce H. Organic Letters, 2011 , vol. 13, # 15 p. 3818 - 3821]

Alkyl-alkenyl cross coupling via alkyl cobaloxime radical chemistry. An alkyl equivalent to the heck reaction compatible with common organic functional groups

[Branchaud, Bruce P.; Meier, Mark S.; Choi, Youngshin Tetrahedron Letters, 1988 , vol. 29, # 2 p. 167 - 170]

More Articles...