3-Halopropenyl esters as precursors of a new class of oxygen-substituted allylic organometallic compounds: Applications in organic synthesis
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| 024 | 7 | 0 | |a 10.1351/pac200476030657 |2 doi |
| 035 | |a (NATIONALLICENCE)gruyter-10.1351/pac200476030657 | ||
| 245 | 0 | 0 | |a 3-Halopropenyl esters as precursors of a new class of oxygen-substituted allylic organometallic compounds: Applications in organic synthesis |h [Elektronische Daten] |c [Marco Lombardo, Sebastiano Licciulli, C. Trombini] |
| 520 | 3 | |a 3-halopropenyl esters, readily prepared by the addition of acyl halides to acrolein, react with zinc, indium, and chromium(II), thus opening a route to a new class of oxygen-substituted allylic organometallic compounds. Indium and zinc reagents smoothly add to carbonyl compounds, affording alk-1-en-3,4-diol derivatives in a variety of synthetic procedures which include typical Grignard stepwise conditions as well as Barbier one-pot protocols. Using zinc and indium in water or aprotic solvents, simple diastereoselectivity was found to depend on the nature of the carbonyl compound; conjugated aldehydes favor formation of syn-adducts while unconjugated aldehydes favor anti-adducts. Moving to chromium, a reversal of regioselectivity was observed in favor of (Z)-4-hydroxy-enolacetates, flexible protected forms of homoaldols. Chromium complexes are generated in a catalytic cycle based on the combined use of the redox Mn(0)/Cr(III) couple and of TMSCl. When the Cr-catalyzed reaction is carried out in the presence of Jacobsen's Salen ligand, the regiochemical outcome of the reaction is again reversed, and syn-alk-1-en-3,4-diols are formed in high ee's. | |
| 540 | |a © 2013 Walter de Gruyter GmbH, Berlin/Boston | ||
| 700 | 1 | |a Lombardo |D Marco |u Dipartimento di Chimica "G.Ciamician ”, University of Bologna, Bologna, Italy |4 aut | |
| 700 | 1 | |a Licciulli |D Sebastiano |u Dipartimento di Chimica "G.Ciamician ”, University of Bologna, Bologna, Italy |4 aut | |
| 700 | 1 | |a Trombini |D C. |u Dipartimento di Chimica "G.Ciamician ”, University of Bologna, Bologna, Italy |4 aut | |
| 773 | 0 | |t Pure and Applied Chemistry |d De Gruyter |g 76/3(2004-01-01), 657-669 |x 0033-4545 |q 76:3<657 |1 2004 |2 76 |o pac | |
| 856 | 4 | 0 | |u https://doi.org/10.1351/pac200476030657 |q text/html |z Onlinezugriff via DOI |
| 908 | |D 1 |a research article |2 jats | ||
| 950 | |B NATIONALLICENCE |P 856 |E 40 |u https://doi.org/10.1351/pac200476030657 |q text/html |z Onlinezugriff via DOI | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Lombardo |D Marco |u Dipartimento di Chimica "G.Ciamician ”, University of Bologna, Bologna, Italy |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Licciulli |D Sebastiano |u Dipartimento di Chimica "G.Ciamician ”, University of Bologna, Bologna, Italy |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Trombini |D C. |u Dipartimento di Chimica "G.Ciamician ”, University of Bologna, Bologna, Italy |4 aut | ||
| 950 | |B NATIONALLICENCE |P 773 |E 0- |t Pure and Applied Chemistry |d De Gruyter |g 76/3(2004-01-01), 657-669 |x 0033-4545 |q 76:3<657 |1 2004 |2 76 |o pac | ||
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| 898 | |a BK010053 |b XK010053 |c XK010000 | ||
| 949 | |B NATIONALLICENCE |F NATIONALLICENCE |b NL-gruyter | ||