Vinylogous aldol products from chiral crotylsilanes obtained by enantioselective Rh(II) and Cu(I) carbenoid Si-H insertion.
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.
Wu
Jie
J
Department of Chemistry, Metcalf Center for Science and Engineering, 590 Commonwealth Avenue, Boston University, Boston, Massachusetts 02215, USA.
Chen
Yu
Y
Panek
James S
JS
D000447:Aldehydes / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D012211:Rhenium / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D012828:Silicones / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D012821:Silanes; D012828:Silicones; C507609:crotylsilane; C030011:carbene; D012211:Rhenium; D003300:Copper; D006859:Hydrogen; C116609:3-hydroxybutanal; D008697:Methane
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