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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 23
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Original Articles

Rh(I)-Catalyzed Asymmetric Hydrosilylation and Hydroboration/Oxidation Reactions Using Berens Ligand

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Pages 4207-4214 | Received 11 Apr 2008, Published online: 31 Oct 2008
 

Abstract

The Berens ligand 2 was used in a number of Rh(I)-catalyzed asymmetric hydrosilylations of acetophenones under standard conditions, affording the corresponding 1-arylalcohols in ees up to 65%. Some novel Rh catalysts were generated in situ from the neutral precatalyst [Rh(µ-Cl)(COD)]2 and screened in the catalytic asymmetric hydroboration/oxidation of styrenes, gave enantioselectivities of up to 62%.

ACKNOWLEDGMENTS

We thank the Fundação para a Ciência e a Tecnologia and Programa Operacional Ciência e Inovação (POCI) for generous financial support of this work (POCI/QUI/55779/2004), including a grant (C.S.M.), which was partly funded by the European Community Fund Fundo Europeu de Desenvolvimento Regional (FEDER).

Notes

a Determined by GC.

b Determined by GC using a Cyclodex B capillary column.

a Standard conditions: vinyl arene/CatBH/ligand/pre-catalyst 1/1.1/0.027/0.013 in THF, rt, ca. 15 h.

b Determined by GC analysis.

c The percentage ee of the branched alcohol was determined by chiral GC analysis (on a cyclosil-B capillary column).

d The major isomer is indicated in parentheses.

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