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Diastereo- and enantioselective synthesis of α,β-disubstituted γ-nisalkoxycarbonyl sulfonates

Enders, D ; Sharif University of Technology | 2009

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  1. Type of Document: Article
  2. DOI: 10.1055/s-0029-1218017
  3. Publisher: 2009
  4. Abstract:
  5. The asymmetric synthesis of ,-disubstituted -bisalkoxycarbonyl sulfonates is reported. The synthesis is based on the Michael addition of a lithiated enantiopure sulfonate bearing a cheap chiral sugar auxiliary to Knoevenagel acceptors. The reaction proceeds with high asymmetric inductions (ds=69-96%) and good yields (62-79%). The absolute configuration was determined by X-ray crystal-structure analysis
  6. Keywords:
  7. Asymmetric synthesis ; Knoevenagel acceptor ; Sugar auxiliary ; Sulfonate ; Dimethyl 2 [2 [5 (2,2 dimethyl 1,3 dioxolan 4 yl) 2,2 dimethyltetrahydrofuro[2,3 d][1,3]dioxo 6 yloxysulfonyl] 2 phenyl 1 4 tolyethyl]malonate ; Sulfonic acid derivative ; Unclassified drug ; Crystal structure ; Diastereoisomer ; Enantioselectivity ; Knoevenagel condensation ; Michael addition ; Substitution reaction ; X ray crystallography
  8. Source: Synlett ; Issue 17 , 2009 , Pages 2872-2874 ; 09365214 (ISSN)
  9. URL: https://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-0029-1218017