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Efficient diastereo- and enantioselective synthesis of α,β-disubstituted γ-phosphono sulfonates

Enders, D | 2009

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  1. Type of Document: Article
  2. DOI: 10.1016/j.tetasy.2009.10.011
  3. Publisher: 2009
  4. Abstract:
  5. The first asymmetric synthesis of α,β-disubstituted γ-phosphono sulfonates is reported. The key step is the Michael addition of a lithiated enantiopure sulfonate bearing an inexpensive chiral sugar auxiliary to α,β-unsaturated phosphonates in good diastereoselectivities. After chromatographic purification, the cleavage of the chiral sugar auxiliary proceeds without any epimerization or racemization to form the corresponding isopropyl sulfonate in very good overall yield (75%) and excellent diastereomeric and enantiomeric excess (de, ee ≥ 95%). © 2009 Elsevier Ltd. All rights reserved
  6. Keywords:
  7. Phosphonium derivative ; Sulfonic acid derivative ; Asymmetric synthesis ; Chirality ; Chromatography ; Diastereoisomer ; Enantiomer ; Enantioselectivity ; Epimerization ; Michael addition ; Priority journal ; Purification ; Quantum yield ; Reaction analysis ; Stereochemistry
  8. Source: Tetrahedron Asymmetry ; Volume 20, Issue 21 , 2009 , Pages 2429-2431 ; 09574166 (ISSN)
  9. URL: https://www.sciencedirect.com/science/article/abs/pii/S0957416609007745