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Enantioselective ester enolate-Claisen

Example 3, Enantioselective ester enolate-Claisen Rearrangement ... [Pg.125]

Some advancement has been described for the development of a catalytic enantioselective ester enolate Claisen rearrangement. The strong Lewis basic carboxylate functionality present in the Claisen product effectively coordinates with Lewis or Bronsted acids prohibiting the catalytic turnover. Corey has reported the use of stoichiometric bromoborane 175 to generate chiral boron enolate which undergoes [3,3]-sigmatropic rearrangement to yield 176. ° Kazmaier relied on excess quinidine 178 to provide for asymmetric induction in the conversion of 177 to amino acid 179. ... [Pg.51]

The rearrangement of ester enolates (Ireland rearrangement)36 41 87,88-91-257,292 467-469 derived from allyl esters is perhaps the most flexible Claisen variation, allowing the diasiereo-and enantioselective controlled synthesis of y.fS-unsaturated acids either by a change of the double-bond configuration of the allylic alcohol moiety or variation of the solvent system. [Pg.112]

See other pages where Enantioselective ester enolate-Claisen is mentioned: [Pg.51]    [Pg.51]    [Pg.578]    [Pg.90]    [Pg.94]    [Pg.499]    [Pg.499]    [Pg.499]    [Pg.264]    [Pg.120]    [Pg.111]    [Pg.179]    [Pg.222]    [Pg.250]    [Pg.128]    [Pg.310]    [Pg.311]    [Pg.179]    [Pg.516]    [Pg.516]    [Pg.519]    [Pg.526]   


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Claisen enantioselective

Enantioselective ester enolate-Claisen rearrangement

Enol esters

Enolates enantioselective

Enolates enol esters

Ester enolate

Esters enolates

Esters enolization

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