Letters in Organic Chemistry

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

DOI: 10.2174/157017810790533887

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

Page: [21 - 26] Pages: 6

  • * (Excluding Mailing and Handling)

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