Studies on Aldol Reactions of Nortropinone Derivatives in Solution and on Solid Phase

Ryszard      Lazny; Aneta      Nodzewska; Michal      Sienkiewicz

doi:10.2174/157017810790533887

Abstract

Polymer-anchored (Merrifield, trityl chloride, Wang p-nitrophenyl carbonate and triazene supports) nortropinone, or N-protected nortropinone derivatives in solution, were subjected to deprotonation with LDA or chiral lithium amides, and the resulting lithium enolates were trapped with an aldehyde. The aldols were obtained with moderate to good yields (44-84%) and enantioselectivities (44-86% ee).

Keywords: Aldol reaction, polymer support, solid-phase synthesis, chiral lithium amide, nortropinone

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Letters in Organic Chemistry

Title: Studies on Aldol Reactions of Nortropinone Derivatives in Solution and on Solid Phase

Volume: 7 Issue: 1

Author(s): Ryszard Lazny, Aneta Nodzewska and Michal Sienkiewicz

Affiliation:

Keywords: Aldol reaction, polymer support, solid-phase synthesis, chiral lithium amide, nortropinone

Abstract: Polymer-anchored (Merrifield, trityl chloride, Wang p-nitrophenyl carbonate and triazene supports) nortropinone, or N-protected nortropinone derivatives in solution, were subjected to deprotonation with LDA or chiral lithium amides, and the resulting lithium enolates were trapped with an aldehyde. The aldols were obtained with moderate to good yields (44-84%) and enantioselectivities (44-86% ee).

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Lazny Ryszard, Nodzewska Aneta and Sienkiewicz Michal, Studies on Aldol Reactions of Nortropinone Derivatives in Solution and on Solid Phase, Letters in Organic Chemistry 2010; 7 (1) . https://dx.doi.org/10.2174/157017810790533887