Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 24, 2007
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Article information


Submitted
22 Aug 2007
Accepted
20 Sep 2007
First published
24 Oct 2007

Org. Biomol. Chem., 2007,5, 3922-3931
Article type
Paper

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

Social activity

Search articles by author

Spotlight

Advertisements