@article{MTMT:1955481,
	title = {Stereoselective synthesis of pinane-type tridentate aminodiols and their application in the enantioselective addition of diethylzinc to benzaldehyde},
	url = {https://m2.mtmt.hu/api/publication/1955481},
	author = {Csillag, Kinga Karola and Németh, Lukács and Martinek, Tamás and Szakonyi, Zsolt and Fülöp, Ferenc},
	doi = {10.1016/j.tetasy.2012.01.020},
	journal-iso = {TETRAHEDRON ASYMMETR},
	journal = {TETRAHEDRON-ASYMMETRY},
	volume = {23},
	unique-id = {1955481},
	issn = {0957-4166},
	abstract = {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.},
	keywords = {DIASTEREOSELECTIVE SYNTHESIS; DIALKYLZINC; Aldehydes; REDUCTION; REARRANGEMENT; KETONES; CHIRAL LIGANDS; ACID-DERIVATIVES; (+)-3-CARENE; ALCOHOL-PROMOTED ADDITION},
	year = {2012},
	eissn = {1362-511X},
	pages = {144-150},
	orcid-numbers = {Martinek, Tamás/0000-0003-3168-8066; Szakonyi, Zsolt/0000-0003-2432-8409; Fülöp, Ferenc/0000-0003-1066-5287}
}