1.1- Iminoalcohols

N-Condensed l,3-N,N-heterocyclic 1,1-iminoalcohols from diketones and o-diamines... 

Polynuclear complexes with aminoalcohols and iminoalcohols as ligands O-bridged and hydrogen bonded species. J. A. Bertrand and P. G. Eller, Prog. Inorg. Chem., 1976, 21, 29-53 (54). 

Bertrand, J. A. and Eller, P. G., Polynuclear Complexes with Aminoalcohols and Iminoalcohols as Ligands Oxygen-Bridged and Hydrogen-Bonded Species 21 29... 

Template synthesis (4.56) was also used to obtain complexes of iminoalcohol derivatives of thiosalicylaldehyde 893 [221-223] ... 

Various types of structures 895 and 896 were obtained with use of transformation (4.58) applied to iminoalcohol derivatives of heterocyclic carbonyl compounds used as ligands [220,225], The structure of 895 [225] and 896 [220] was proved by x-ray analysis ... 

According to Baldwin s rules [76JCS(CC)234 92MI1 93ACR476], the cyclization 1A — IB, as a 5-endo-trig process, is disallowed. But despite these rules, the transformation 1A — IB is rather fast. Thus, the rate constant of the monomolecular cyclization of iminoalcohol 1A (R1 = H R2 = Me R3 = Ph), for example, has been estimated as k > 0.06 s 1... 

Retrosynthetic cleavage of the carbon-oxygen bond in generalised oxazole 3.10 produces iminoalcohol 3.11 (better represented in the amide form... 

Disconnection of the C5-oxygen bond in 8.16 leads to iminoalcohol 8.17 which occurs as amide 8.18. Cleavage of the amide linkage leads to an activated carboxylic acid 8.20 plus the heteroatom-containing amidoxime 8.19. 

The 2-amino-2-methyl-l-propanol used was the Practical grade obtained from the Eastman Kodak Company. This iminoalcohol can also be secured from the Commercial Solvents ( orporation. 

The most effective route to aminoalcohol (493) was established by screening various stereochemically homogeneous N,N-disubstituted-, N-monosubstitut-ed-amino alcohols and iminoalcohols as chiral additives to promote asymmetric addition of alkylzinc to N-diphenylphosphinoyl imine (492). The addition reactions that were performed in the presence of this compound resulted in excellent enantioselectivity (Figure 94a). 

Proposed reaction mechanism of l-hydroxy-2-propanone or l-hydroxy-2-butanone with ammonium sulfide is shown in Figure 5. 2-Iminoalcohols, which were derived from the reaction of ammonia and a-hydroxyketones, were condensed with another molecule of a-hydroxyketone to form 2-(l-hydroxymethyl)-2,4-dialkyl-3-oxazolines. The substitution of -OH group with -SH group resulted in the formation of 2-(l-hydroxyemthyl)-2,4-dialkyl-3-thiazolines. No 2-(l-mercaptomethyl)-substituted isomers were found in either reaction. Upon heating, these intermediates were further converted to the corresponding oxazolines, oxazoles, thiazolines and thiazoles. 

Hassner and co-workers reported the cleavage of isoxazolines 283 (derived from INOC reaction of oximes) using Raney Ni to afford unsaturated nitriles 286 or ketoalcohols 285 (Scheme 66) [168]. Some of the derivatives of isoxazolines 283 led to amino azasugars that were glycosidase inhibitors. The reactions in Scheme 66 presumably proceed through the iminoalcohol 284 which on hydrolysis provides the hydroxyketone 285. On the other hand. 

More recently chelate derivatives of iminoalcohols were found to be dimeric with planar Zh2N2 four-membered rings [EtZnOC(NEt2)CH2NBu ]2, 21, has been investigated by X-ray diffraction [40]. 

Spiro-1,1-aminoethers from cyclic iminoalcohols via cyclic N-chlorimino-alcohols—Stereospecific ring closure—Steroidal alkaloids s. 19, 337... 

N-Condensed oxazolidine ring from cyclic 2-iminoalcohols... 

Formic acid Cyclic a-aminoketones from cyclic tert. 2-iminoalcohols with ring expansion s. 18, 781 HCOOH Q... 

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