Indium mediated allylation and propargylation reactions of dimethyl acetals and ketals
JS Kwon, AN Pae, KI Choi, HY Koh, Y Kim, YS Cho
Index: Kwon, Jin Sun; Pae, Ae Nim; Choi, Kyung Il; Koh, Hun Yeong; Kim, Youseung; Cho, Yong Seo Tetrahedron Letters, 2001 , vol. 42, # 10 p. 1957 - 1959
Full Text: HTML
Citation Number: 44
Abstract
Indium mediated allylation and propargylation reactions of acetals and ketals with various allyl or propargyl bromides in aqueous media successfully provided the corresponding homoallylic or homopropargylic (and allenylic) alcohol, respectively, in moderate to good yields. Highly chemoselective allylation is also described. The ketal and aryl acetal could be selectively allylated over the aliphatic one in 80–84% yields.
Related Articles:
Electrochemical allylation of carbonyl compounds using nickel catalyst and zinc (II) species
[Durandetti, Sylvie; Sibille, Soline; Perichon, Jacques Journal of Organic Chemistry, 1989 , vol. 54, # 9 p. 2198 - 2204]
A new method of the zinc promoted transformation of carbonyl compounds to homoallylic alcohols.
[Shono, Tatsuya; Ishifune, Manabu; Kashimura, Shigenori Chemistry Letters, 1990 , # 3 p. 449 - 452]
[Alonso, Emma; Guijarro, David; Yus, Miguel Tetrahedron, 1995 , vol. 51, # 42 p. 11457 - 11464]
[Volla, Chandra M. R.; Markovic, Dean; Laclef, Sylvain; Vogel, Pierre Chemistry - A European Journal, 2010 , vol. 16, # 30 p. 8984 - 8988]
[Takaki, Ken; Kusudo, Takeshi; Uebori, Shinya; Nishiyama, Tetsushi; Kamata, Tohru; Yokoyama, Masaki; Takehira, Katsuomi; Makioka, Yoshikazu; Fujiwara, Yuzo Journal of Organic Chemistry, 1998 , vol. 63, # 13 p. 4299 - 4304]