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2005
Enantioselective syntheses
O 0031
Rhodium-Catalyzed Asymmetric 1,4-Addition of Alkenylsilanes Generated by
of Alkynes: A One-Pot Procedure Where a Rhodium/(S)-Binap
03- 038 Hydrosilylation
Complex Catalyzes the Two Successive Reactions. — Hydrosilylation of the
alkynes (I) in the presence of a chiral rhodium/BINAP catalyst gives the corresponding
alkenylsilanes. They undergo asymmetric 1,4-addition to cyclic α,β-unsaturated ketones such as (II) to give the alkenylated products (III) with up to 98% e.e. Although
the intermediate alkenylsilanes are formed as mixtures of regio- and E/Z-isomers, the
terminal alkenylsilanes are much more reactive than the internal isomers giving the
1,4-addition products with high chemoselectivity. — (OTOMARU, Y.; HAYASHI*,
T.; Tetrahedron: Asymmetry 15 (2004) 17, 2647-2651; Dep. Chem., Grad. Sch. Sci.,
Kyoto Univ., Sakyo, Kyoto 606, Japan; Eng.) — Kieslich
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