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Issue 24, 2007
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Asymmetric synthesis of β-amino-γ-substituted-γ-butyrolactones: double diastereoselective conjugate addition of homochiral lithium amides to homochiral α,β-unsaturated esters

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Abstract

Chiral α,β-unsaturated esters, containing a single, γ-stereogenic centre, show modest levels of substrate control upon conjugate addition of lithium dibenzylamide. Double diastereoselective conjugate additions of homochiral lithium N-benzyl-N-(α-methylbenzyl)amide to the homochiral α,β-unsaturated esters display “matching” and “mismatching” effects. In each case, however, these additions proceed under the dominant stereocontrol of the lithium amide to give the corresponding β-amino esters in high de. A remarkable reversal in stereoselectivity is noted by changing the ester functionality to an oxazolidinone. Subsequent O-deprotection and cyclisation of the resultant β-amino adducts gives access to the corresponding β-amino-γ-substituted-γ-butyrolactones in good yield and high de.

Graphical abstract: Asymmetric synthesis of β-amino-γ-substituted-γ-butyrolactones: double diastereoselective conjugate addition of homochiral lithium amides to homochiral α,β-unsaturated esters

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Publication details

The article was received on 22 Aug 2007, accepted on 20 Sep 2007 and first published on 24 Oct 2007


Article type: Paper
DOI: 10.1039/B712937H
Citation: Org. Biomol. Chem., 2007,5, 3922-3931
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    Asymmetric synthesis of β-amino-γ-substituted-γ-butyrolactones: double diastereoselective conjugate addition of homochiral lithium amides to homochiral α,β-unsaturated esters

    T. Cailleau, J. W. B. Cooke, S. G. Davies, K. B. Ling, A. Naylor, R. L. Nicholson, P. D. Price, P. M. Roberts, A. J. Russell, A. D. Smith and J. E. Thomson, Org. Biomol. Chem., 2007, 5, 3922
    DOI: 10.1039/B712937H

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