Vinylogous Aldol Products from Chiral Crotylsilanes Obtained by Enantioselective Rh(II) and Cu(I) Carbenoid Si−H Insertion

Enantioenriched homoallylic ethers containing a α,β-unsaturated ester (syn-vinylogous aldol products) were directly accessed by Lewis acid catalyzed crotylation utilizing chiral silane 2. The reagents were prepared by enantioselective Si−H insertion to an α-diazovinylacetates using Davies’ Rh2(DOSP)...

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Bibliographic Details
Published in:Organic letters 2010-05, Vol.12 (9), p.2112-2115
Main Authors: Wu, Jie, Chen, Yu, Panek, James S.
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Copper - chemistry
Hydrogen - chemistry
Methane - analogs & derivatives
Methane - chemistry
Rhenium - chemistry
Silanes - chemistry
Silicones - chemistry
Stereoisomerism
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Summary:Enantioenriched homoallylic ethers containing a α,β-unsaturated ester (syn-vinylogous aldol products) were directly accessed by Lewis acid catalyzed crotylation utilizing chiral silane 2. The reagents were prepared by enantioselective Si−H insertion to an α-diazovinylacetates using Davies’ Rh2(DOSP)4 catalyst or chiral Cu(I) Schiff base complex.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/ol100604m