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Ireland–Claisen rearrangement

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Chemical reaction

TheIreland–Claisen rearrangement is achemical reaction of anallylic ester with strong base to give an γ,δ-unsaturatedcarboxylic acid.^[1]^[2]^[3]

Several reviews have been published.^[4]^[5]^[6]

The Ireland–Claisen rearrangement is a type ofClaisen rearrangement. The mechanism is therefore a concerted[3,3]-sigmatropic rearrangement which according to theWoodward–Hoffmann rules show a concerted,suprafacial,pericyclic reaction pathway.

^Ireland, R. E.; Mueller, R. H. (1972). "Claisen rearrangement of allyl esters".J. Am. Chem. Soc.94 (16): 5897.doi:10.1021/ja00771a062.
^Ireland, R. E.; Mueller, R. H.; Willard, A. K. (1976). "The ester enolate Claisen rearrangement. Stereochemical control through stereoselective enolate formation".J. Am. Chem. Soc.98 (10):2868–2877.doi:10.1021/ja00426a033.
^Miller, S. P.; Morken, J. P. (2004). "Catalytic Diastereoselective Reductive Claisen Rearrangement".Organic Letters.60 (16):2743–2745.doi:10.1021/ol026273b.PMID 12153224.
^Ziegler, F. E. (1977). "Stereo- and regiochemistry of the Claisen rearrangement: Applications to natural products synthesis".Acc. Chem. Res.10 (6):1423–1452.doi:10.1021/ar50114a006.
^Pereira, S.; Srebnik, M. (1993)."The Ireland–Claisen rearrangement"(PDF).Aldrichimica Acta.26 (1):17–29. Archived fromthe original(PDF) on 2014-02-19. Retrieved2014-01-25.
^Chai, Y.; Hong, S.; Lindsay, H. A.; McFarland, C.; McIntosh, M. C. (2002). "New aspects of the Ireland and related Claisen rearrangements".Tetrahedron.58 (15):2905–2928.doi:10.1016/S0040-4020(02)00164-3.

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