TY  - JOUR
AU  - Csillag, Kinga Karola
AU  - Németh, Lukács
AU  - Martinek, Tamás
AU  - Szakonyi, Zsolt
AU  - Fülöp, Ferenc
TI  - Stereoselective synthesis of pinane-type tridentate aminodiols and their application in the enantioselective addition of diethylzinc to benzaldehyde
JF  - TETRAHEDRON-ASYMMETRY
J2  - TETRAHEDRON ASYMMETR
VL  - 23
PY  - 2012
IS  - 2
SP  - 144
EP  - 150
PG  - 7
SN  - 0957-4166
DO  - 10.1016/j.tetasy.2012.01.020
UR  - https://m2.mtmt.hu/api/publication/1955481
ID  - 1955481
N1  - WC: Chemistry, Inorganic & Nuclear; Chemistry, Organic; Chemistry, Physical
Funding Agency and Grant Number: Hungarian Research FoundationOrszagos Tudomanyos Kutatasi Alapprogramok (OTKA) [OTKA NK81371, TAMOP-4.2.1/B-09/1/KONV-2010-0005]; Bolyai Janos FellowshipHungarian Academy of Sciences
            Funding text: We are grateful to the Hungarian Research Foundation (OTKA NK81371) and TAMOP-4.2.1/B-09/1/KONV-2010-0005 for financial support and acknowledge the receipt of a Bolyai Janos Fellowship for Zsolt Szakonyi. Tamas A. Martinek acknowledges HAS Lendulet Foldamer research group.
CAplus AN 2012:381772 (Journal);
AB  - 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.
LA  - English
DB  - MTMT
ER  -