Asymmetric Synthesis of syn- and anti-1,3-Amino Alcohols
- 14 May 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (23) , 6518-6519
- https://doi.org/10.1021/ja026292g
Abstract
The first application of metalloenamines derived from N-sulfinyl imines is reported for the highly diastereoselective addition to aldehydes. Reduction of the β-hydroxy-N-sulfinyl imine products with catecholborane and LiBHEt3 provides syn- and anti-1,3-amino alcohol derivatives, respectively, with very high diastereomeric ratios.Keywords
This publication has 14 references indexed in Scilit:
- A facile three-step synthesis of 1,2-amino alcohols using the Ellman homochiral tert-butylsulfinamideTetrahedron Letters, 2001
- Asymmetric synthesis of pre-protected α,α-disubstituted amino acids from tert-butanesulfinyl ketiminesTetrahedron Letters, 2001
- Asymmetric Synthesis of α,α-Dibranched Amines by the Trimethylaluminum-Mediated 1,2-Addition of Organolithiums to tert-Butanesulfinyl KetiminesJournal of the American Chemical Society, 1998
- Asymmetric synthesis of amino acids using sulfinimines (thiooxime S-oxides)Chemical Society Reviews, 1998
- Synthesis of Complex Nucleoside AntibioticsChemical Reviews, 1995
- MetalloenaminesPublished by Elsevier ,1991
- Studies directed toward the total synthesis of lonomycin A (emericid). Asymmetric synthesis of the C1-C11 synthonThe Journal of Organic Chemistry, 1990
- 1,1-Di-tert-butyldiazeneJournal of the American Chemical Society, 1982
- Direct conversion of nitriles to .alpha.-alkylated aldehydesThe Journal of Organic Chemistry, 1981
- Total syntheses of negamycin and the antipodeJournal of the American Chemical Society, 1972