Vinylogous aldol products from chiral crotylsilanes obtained by enantioselective Rh(II) and Cu(I) carbenoid Si-H insertion.

Org Lett

Department of Chemistry, Metcalf Center for Science and Engineering, 590 Commonwealth Avenue, Boston University, Boston, Massachusetts 02215, USA.

Published: May 2010

Enantioenriched homoallylic ethers containing a alpha,beta-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 alpha-diazovinylacetates using Davies' Rh(2)(DOSP)(4) catalyst or chiral Cu(I) Schiff base complex.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3164278PMC
http://dx.doi.org/10.1021/ol100604mDOI Listing

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