1,10,10-Trimethyl-5-phenyl-3-oxa-4-azatricyclo[5.2.1.02,6]dec-4-en-2-ol (original) (raw)
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( E )-3-(1-Naphthylamino)methylene-(+)-camphor
Acta Crystallographica Section E Structure Reports Online, 2011
Key indicators: single-crystal X-ray study; T = 160 K; mean (C-C) = 0.007 Å; R factor = 0.059; wR factor = 0.155; data-to-parameter ratio = 7.4.
NMR elucidation of novel ligands derived from (R)-(+)-camphor
Structural Chemistry, 2009
The complete NMR elucidation of five camphor-derived ligands is reported. 2D NMR techniques such as NOESY are used to assist in the determination of the orientation of the donor groups in space. The compounds were synthesized as ligands to be used in asymmetric catalysis. They represent the first instance where both donor groups are pendant on the C3 position of the camphor skeleton. The single crystal X-ray structure of one of the ligands was obtained and was helpful in determining the potential NOESY interactions within the molecule. For the other ligands, density functional theory (DFT) optimizations was performed [B3LYP/6-31?g(d)] to visualize possible NOE interactions.
Tetrahedron-asymmetry, 2005
The tandem [4+2]/[3+2] cycloaddition of nitroalkenes has been employed in the synthesis of 1-azafenestranes, molecules of theoretical interest because of planarizing distortion of their central carbon atoms. The synthesis of c,c,c,c-[5.5.5.5]-1-azafenestrane was completed in good yield from a substituted nitrocyclopentene, and its borane adduct was analyzed through X-ray crystallography, which showed a moderate distortion from ideal tetrahedral geometry. The syntheses of two members of the [4.5.5.5] family of 1-azafenestranes are also reported, including one with a trans fusion at a bicyclic ring junction which brings about considerable planarization of one of the central angles (16.8°deviation from tetrahedral geometry). While investigating the [4.5.5.5]-1-azafenestranes, a novel dyotropic rearrangement that converts nitroso acetals into tetracyclic aminals was discovered. Through conformational analysis, a means to prevent this molecular reorganization was formulated and realized experimentally with the use of a bulky vinyl ether in the key [4+2] cycloaddition reaction. Finally, DFT calculations on relative strain energy for the 1-azafenestranes, as well as their predicted central angles, are disclosed.
New camphor derived chiral ligands for asymmetric synthesis
Tetrahedron: Asymmetry, 1998
New enantiomerically pure 1,4-diols and 1,4-aminoalcohols have efficiently been prepared in one and two steps, respectively, from a commercially available camphor derived exo fused lactone. Using sterically hindered amines, an aldol addition of two lactone molecules was observed and the stereochemistry of the products was determined by X-ray crystallography.
A new chiral oxazoline derived from camphor and its conversion to (R)-2-methylalkanoic acids
Tetrahedron: Asymmetry, 2000
(1S,5R,7R)-(^)-10,10-Dimethyl-3-ethyl-4-oxa-2-azatricyclo[5.2.1.0 1,5 ]dec-2-ene 2 was prepared in 95% yield from (1S)-1-amino-2-exo-hydroxyapocamphane 1. The chiral oxazoline could be alkylated (LDA/ THF/^78 C/RX, RX=ethyl, n-propyl, n-butyl iodides or benzyl bromide) to 3 in 95% yield and >95% diastereoselectivity, and the products hydrolysed to (R)-2-methylalkanoic acids 4 (43±47% yield, 93±98% e.e.).
Acta Crystallographica Section E-structure Reports Online, 2014
Structure of Organic Compound (E)-3-((S)1-Phenylethylamine)methylene R (+) Camphor
Crystallography Reports, 2020
The synthesis and crystal structure of (E)-3-((S)-1-phenylethylamine)methylene R-(+) camphor are discussed. The 1 H NMR spectrum in a chloroform solution indicates the existence of a mixture of two tautomers, the main tautomer corresponds to the E-isomer. On the other hand, in the solid state, the crystal structure solved by X-ray diffraction shows only the occurrence of this latter form. Crystal data: monoclinic (P2 1), a = 11.019(4) Å, b = 6.782(2) Å, c = 11.186(4) Å, β = 101.843(4)°.