Enamine??Mediated Addition of Aldehydes to Cyclic Enones

…, S Insogna, J Overgaard, M Bella

Index: Schietroma, Daniele M. Scarpino; Monaco, Mattia R.; Visca, Valerio; Insogna, Susanna; Overgaard, Jacob; Bella, Marco Advanced Synthesis and Catalysis, 2011 , vol. 353, # 14-15 p. 2648 - 2652

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Citation Number: 5

Abstract

The O-trimethylsilylated α,α-diphenylprolinol-catalyzed addition of aldehydes to cyclic unsaturated enones is described. The apparently unusual stereochemical outcome is discussed. ... Table 1. Screening of catalysts for the addition of capronaldehyde 2a to enone 1a. ... [a] Reaction conditions: 0.3 mmol 1a, 0.6 mmol 2a, 2 mL toluene; 10 mol% organocatalyst I–VII; −20 °C, 24–72 h. ... [c] The ee and dr values determined by CSP-GC, utilizing a β-dex column; ...