Direct Reductive Amination of Aldehydes and Ketones Using Phenylsilane: Catalysis by Dibutyltin Dichloride

Organic Letters

Volumn 3, Issue 11, 2001, Pages 1745-1748

  Apodaca, Richard ^a   Xiao, Wei ^a  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

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ARTICLE;

EID: 0000899213     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015948s     Document Type: Article

References (36)

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30. General experimental procedure: A solution of carbonyl compound (1.5 mmol, 1 equiv) in tetrahydrofuran (0.3 mL) was treated with an amine (1.5 mmol, 1 equiv), followed by dibutyltin dichloride (9 mg, 0.03 mmol, 0.02 equiv). After 1-2 min at room temperature, the resulting mixture was treated with organosilane (1.7 mmol, 1.1 equiv). Upon completion, the reaction was diluted with chromatography solvent (with added dichloromethane or ethyl acetate to dissolve solid material) and chromatographed.
31. THF was selected as a solvent because of its ability to form concentrated solutions with a variety of potential substrates.
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35. 2 itself or a hydrolysis product, cannot be ruled out.
36. 13C NMR.