A High Yielding One-Pot Synthesis of Allylic-Vinylic Alcohols: The Adducts of Tetraallylstannane and α,β-Unsaturated Carbonyl Compounds

Autor: Sarah K. Leitch, Adam McCluskey
Rok vydání: 2003
Předmět:
Zdroj: ChemInform. 34
ISSN: 1522-2667
0931-7597
Popis: The reaction of α,β-unsaturated aldehydes with tetra-allystannane (1, 0.25 equivalents) results in regioselective 1,2-addition to generate the corresponding allylic-vinylic alcohols in good to excellent yields (> 90%). Reactions with the equivalent ketones also proceed well (15-91%j although requiring more forcing conditions. Under these conditions, a second reaction pathway was evident for ketones that were less substituted at C3, namely that of methanolysis at C3. In all instances these reactions are elegant in their simplicity and show high levels of atom efficiency not typically found in similar methodologies for the synthesis of allylic-vinylic alcohols.
Databáze: OpenAIRE
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