Rhodium(I)-catalyzed enantioselective 1,4-addition of nucleophilic silicon
A rhodium(I)-catalyzed activation of a silicon-boron linkage, that is, the transmetalation of silicon from boron to rhodium(I) by means of an RhI-OH complex, enables the conjugate transfer of nucleophilic silicon onto α,β-unsaturated acceptors. Pre- or in situ formed cationic rhodium(I)-binap complexes catalyze this novel carbon-silicon bond formation with exceptional enantiocontrol, 92 to >99% ee for cyclic carbonyl and carboxyl compounds as well as >99% ee for acyclic carboxyl compounds.
Walter, Christian,Fr?hlich, Roland,Oestreich, Martin
scheme or table
p. 5513 - 5520
(2009/12/09)
Catalytic asymmetric C-Si bond formation to acyclic α,β- unsaturated acceptors by RhI-catalyzed conjugate silyl transfer using a Si-B linkage
(Chemical Equation Presented) A perfect match: The RhI-catalyzed conjugate silylation of acyclic Z-configured α,β-unsaturated carboxyl compounds including imides with silylboronic ester yields almost enantiopure α-chiral quaternary silanes (see scheme; R=aryl and (branched) alkyl, cod=cycloocta-1,5-diene, pin=pinacolato).
Walter, Christian,Oestreich, Martin
supporting information; experimental part
p. 3818 - 3820
(2009/02/07)
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