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Catalytic asymmetric synthesis of secondary alcohols using chiral cis-1-amino-2-hydroxy-1,2,3,4-tetrahydronaphthalene as chiral ligand

✍ Scribed by Cristina M Bellucci; Antonio Bergamini; Pier Giorgio Cozzi; Angelo Papa; Emilio Tagliavini; Achille Umani-Ronchi

Publisher: Elsevier Science
Year: 1997
Tongue: English
Weight: 529 KB
Volume: 8
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(97)00061-x

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✦ Synopsis

The synthesis and resolution of cis-1-amino-2-hydroxy-1,2,3,4tetrahydronaphthalene 5 by a simple and straightforward methodology has been achieved. The homochiral aminoalcohol has been used in the catalytic reduction of ketones by means of BH 3 .SMe2 affording secondary alcohols in high enantiomeric excesses. On the contrary low enantiomeric excesses have been obtained when (1S,2R)-N,N-dibutyl-lamino-2-hydroxytetrahydronaphthalene 11 has been used to catalyze the enantioselective addition of Et2Zn to benzaldehyde.

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