Tetrahedron Asymmetry p. 895 - 902 (1997)
Update date:2022-08-10
Topics:
Bellucci, Cristina M.
Bergamini, Antonio
Cozzi, Pier Giorgio
Papa, Angelo
Tagliavini, Emilio
Umani-Ronchi, Achille
The synthesis and resolution of cis-1-amino-2-hydroxy-1,2,3,4-tetrahydronaphthalene 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 BH3 · SMe2 affording secondary alcohols in high enantiomeric excesses. On the contrary low enantiomeric excesses have been obtained when (1S,2R)-N,N-dibutyl-1-amino-2-hydroxytetrahydronaphthalene 11 has been used to catalyze the enantioselective addition of Et2Zn to benzaldehyde.
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