relation: http://publicatio.bibl.u-szeged.hu/10398/
title: Stereoselective synthesis of pinane-type tridentate aminodiols and their application in the enantioselective addition of diethylzinc to benzaldehyde
creator:  Csillag Kinga Karola
creator:  Németh Lukács
creator:  Martinek Tamás
creator:  Szakonyi Zsolt
creator:  Fülöp Ferenc
description: A library of pinane-based aminodiols were prepared from commercially available (1R)-(-)-myrtenol (-)-1. Compound (-)-1 was transformed into ally! trichloroacetamide (+)-2 via the acetimidate, followed by the Overman rearrangement. In order obtain the aminodiol structure, (+)-2 was subjected to stereoselective dihydroxylation with OsO4, resulting in dihydroxy trichloroacetamide (+)-3. The trichloroacetyl group was removed from (+)-3 with aqueous HCl and the (1R,2R,3S,5R)-3-amino-2-hydroxymethyl-6,6-dimethylbicyclo[3.1.1]heptan-2-ol hydrochloride (-)-4 obtained was transformed to primary, secondary and tertiary aminodiols by reductive amination, N-alkylation of aminodiol (+)-9 and debenzylation of N-benzyl aminodiol (+)-10, respectively. In the reactions of (+)-9 and (+)-14 with formaldehyde, highly regioselective ring closure was observed. In contrast with earlier results, the aminodiols gave pinane-fused oxazolidines (+)-11 and (-)-15. The aminodiols and their oxazolidine derivatives 5-15 were applied as chiral catalysts in the enantioselective addition of diethylzinc to benzaldehyde. The best enantioselectivity was observed in the case of the N-benzyl-substituted derivative (+)-9. (C) 2012 Elsevier Ltd. All rights reserved.
date: 2012
type: Folyóiratcikk
type: PeerReviewed
format: text
identifier: http://publicatio.bibl.u-szeged.hu/10398/1/1_s2.0_S0957416612000900_main_u.pdf
identifier:     Csillag Kinga Karola;  Németh Lukács;  Martinek Tamás;  Szakonyi Zsolt;  Fülöp Ferenc: Stereoselective synthesis of pinane-type tridentate aminodiols and their application in the enantioselective addition of diethylzinc to benzaldehyde.   TETRAHEDRON-ASYMMETRY, 23 (2).  pp. 144-150.  ISSN 0957-4166 (2012)     
identifier: doi:10.1016/j.tetasy.2012.01.020
relation: 1955481
language: eng
relation: info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetasy.2012.01.020
rights: info:eu-repo/semantics/restrictedAccess