Asymmetric Synthesis of Protected 1,2-Amino Alcohols Using tert-Butanesulfinyl Aldimines and Ketimines
- 29 November 2001
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 66 (26) , 8772-8778
- https://doi.org/10.1021/jo0156868
Abstract
tert-Butanesulfinyl aldimines and ketimines bearing an α-benzyloxy or α-silyloxy substituent serve as precursors in the synthesis of protected 1,2-amino alcohols in high yields and diastereoselectivities. General protocols are described for the addition of unbranched alkyl, branched alkyl, and aryl organometallic reagents to N-sulfinyl aldimines 1 and 2 and ketimines 5 and 6. Furthermore, the selective N- or O-deprotection of sulfinamide products 3, 4, 7, and 8 is described, enabling further synthetic transformations of the reaction products.Keywords
This publication has 13 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
- A General Synthesis of Enantiopure 1,2-Aminoalcohols via Chiral MorpholinonesTetrahedron, 2000
- One-pot asymmetric synthesis of tert-butanesulfinyl-protected amines from ketones by the in situ reduction of tert-butanesulfinyl ketiminesTetrahedron Letters, 1999
- 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
- Synthesis of chiral, nonracemic methyleneaziridines derived from β-amino alcoholsTetrahedron: Asymmetry, 1996
- Switchover of diastereofacial selectivity in the condensation reaction of optically active N-sulfinimine with ester enolateTetrahedron Letters, 1996
- A convenient reduction of amino acids and their derivativesThe Journal of Organic Chemistry, 1993
- Preparation of acetylenic diethyl acetals from the ortho ester HC(OEt)2OPhThe Journal of Organic Chemistry, 1984
- Experimentelle Prüfung von approximativen Chiralitätsfunktionen [1, 2] am Beispiel der induziert cholesterischen Lösung chiraler Methan‐DerivateBerichte der Bunsengesellschaft für physikalische Chemie, 1978