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Efficient and general asymmetric syntheses of (R)-chroman-4-amine salts

✍ Scribed by Eric A. Voight; Jerome F. Daanen; Steven M. Hannick; Bhadra H. Shelat; Francis A. Kerdesky; Daniel J. Plata; Michael E. Kort

Book ID: 104098297
Publisher: Elsevier Science
Year: 2010
Tongue: French
Weight: 469 KB
Volume: 51
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2010.09.006

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✦ Synopsis

Starting from a variety of substituted chroman-4-ones, a highly enantioselective CBS reduction using in situ-generated B-H catalyst gave (S)-chroman-4-ols. Azide inversion and reduction gave crude (R)chroman-4-amines, which could be purified without chromatography by isolation as the (R)-mandelic or D-tartaric acid salts with good yields and excellent ee.

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