Stereocontrolled route to the synthesis of (+/-)-3-amino-2,2-dimethyl-1,3-diphenylpropan-1-ol

TitleStereocontrolled route to the synthesis of (+/-)-3-amino-2,2-dimethyl-1,3-diphenylpropan-1-ol
Publication TypeJournal Article
Year of Publication2010
AuthorsPatil, MN, Bhowmick, KC, Joshi, NN
JournalTetrahedron Letters
Volume51
Issue45
Pagination5927-5929
Date PublishedNOV
ISSN0040-4039
Keywords1, 3-Aminoalcohol, Aldol-Tishchenko reaction, beta-Hydroxy oxime, Diastereoslective reduction
Abstract

Both the diastereomers of (+/-)-3-amino-2,2-dimethyl-1,3-diphenylpropan-1-ol were synthesized starting from a common intermediate, namely,B-hydroxy, oxime 6. Diastereoselective reduction with NaBH(4)/TiCl(4) and H(2)-Pd/C provided syn- and anti-isomers, respectively. Good overall yield and selectivity were realized using a simple protocol. (C) 2010 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tetlet.2010.09.011
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)2.618
Divison category: 
Organic Chemistry