Asymmetric synthesis of beta-substituted Baylis-Hillman products via lithium amide conjugate addition

Alexander Chernega, Stephen G. Davies, Dirk. L. Elend, Christian A. P. Smethurst, Paul M. Roberts, Andrew D. Smith, G. Darren Smyth

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

A three-step protocol for the asymmetric synthesis of a range of beta-substituted Baylis-Hillman products has been developed. This procedure involves the diastereoselective conjugate addition of lithium (R)-N-methyl-N-(alpha-methylbenzyl) amide to an alpha, beta-unsaturated ester to generate an N-protected beta-amino ester in high de. Subsequent asymmetric aldol reaction via deprotonation with LDA, transmetallation with B(OMe)(3) and addition of an aldehyde gives a range of syn-aldol products in moderate to high de. Purification of the syn-aldol products to homogeneity followed by tandem N-oxidation and Cope elimination gives the desired b-substituted Baylis-Hillman products in good yield and high de and ee. (C) 2007 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)7036-7046
Number of pages11
JournalTetrahedron
Volume63
Issue number30
DOIs
Publication statusPublished - 23 Jul 2007

Keywords

  • CARBON BOND-FORMATION
  • COPE ELIMINATION
  • AMINO ALDEHYDES
  • ALDOL REACTION
  • PRESSURE
  • ADDUCTS
  • ESTERS
  • 4-OXOAZETIDINE-2-CARBALDEHYDES
  • EQUIVALENTS
  • CYCLIZATION

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