Carbon-carbon bond-forming enantioselective synthesis of chiral organosilicon compounds by rhodium/chiral diene-catalyzed asymmetric 1,4-addition reaction.
[reaction: see text] A new synthetic method for chiral organosilicon compounds through a rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to beta-silyl alpha,beta-unsaturated carbonyl compounds has been developed. By employing (R,R)-Bn-bod* as a ligand, a range of arylboronic acids can be coupled with these substrates in very high enantiomeric excess. The resulting beta-silyl 1,4-adducts can be converted to beta-hydroxy carbonyl compounds or allylsilanes while retaining their stereochemical information.
Shintani
Ryo
R
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.
Okamoto
Kazuhiro
K
Hayashi
Tamio
T