Synthesis

Palladium-catalyzed silastannation of secondary propargylic alcohols and their derivatives

TE Nielsen, S Le Quement, D Tanner

Index: Nielsen, Thomas E.; Le Quement, Sebastian Le; Tanner, David Synthesis, 2004 , # 9 p. 1381 - 1390

Full Text: HTML

Citation Number: 20

Abstract

Abstract A series of terminal propargylic alcohols and their derivatives were subjected to Pd- catalyzed silastannation. In all reactions, complete regio-and stereoselectivities were observed with the tributyltin moiety exclusively adding to the internal carbon of the triple bond in a cis fashion, including the first example of a diyne bis-silastannation. Silastannation reaction products could sequentially be protiodesilylated or iododestannylated, thus ...

Related Articles:

Coupling–Isomerization synthesis of chalcones

[Braun, Roland U.; Ansorge, Markus; Mueller, Thomas J. J. Chemistry - A European Journal, 2006 , vol. 12, # 35 p. 9081 - 9094]

Organotin nucleophiles. 5. Palladium-catalyzed allylic propargylation with allenylstannane

[Keinan, Ehud; Peretz, Moshe Journal of Organic Chemistry, 1983 , vol. 48, # 26 p. 5302 - 5309]

Reactivity of 3-silyloxy-1, 4-enynes: Gold (III)-catalyzed regioselective nucleophilic substitution

[Haug, Timm T.; Harschneck, Tobias; Duschek, Alexander; Lee, Chang-Uk; Binder, Joerg T.; Menz, Helge; Kirsch, Stefan F. Journal of Organometallic Chemistry, 2009 , vol. 694, # 4 p. 510 - 514]

More Articles...