129872-11-3Relevant articles and documents
A simple and inexpensive method for the preparation of imines and azadienes
Saoudi,Benguedach,Benhaoua
, p. 2349 - 2354 (1995)
A number of imines and azadienes were prepared in high yield and good purity by using the condensation reactions of various aldehydes and ketones with amines over natural Algerian bentonite.
Efficient synthesis of 2,6,9-triazabicyclo[3.3.1]nonanes through amine-mediated formal [4+4] reaction of unsaturated imines
Tanaka, Katsunori,Siwu, Eric R. O.,Hirosaki, Shinji,Iwata, Takayuki,Matsumoto, Risa,Kitagawa, Yasutaka,Okumura, Mitsutaka,Fukase, Koichi,Pradipta, Ambara R.
, p. 5899 - 5902,4 (2012)
Formal [4+4] reaction of the unsaturated benzyl- or allylimines, which is efficiently mediated by primary amine, provides the 2,6,9-triazabicyclo[3.3.1] nonane derivatives. Variously substituted homo- and hetero-coupling products are obtained in good to excellent yields by quite a simple procedure under mild conditions: by mixing the unsaturated aldehydes with the amines at room temperature.
Understanding α,β-unsaturated imine formation from amine additions to α,β-unsaturated aldehydes and ketones: An analytical and theoretical investigation
Calow, Adam D. J.,Carbó, Jorge J.,Cid, Jessica,Fernández, Elena,Whiting, Andrew
supporting information, p. 5163 - 5172 (2014/06/23)
A combination of in situ IR spectroscopy (ReactIR) and DFT calculations have been used to understand what factors govern the selectivity in the addition of primary amines to α,β-unsaturated aldehydes and ketones, i.e., 1,2- versus 1,4-addition. It has been found that the 1,2-addition products (α,β-unsaturated imines following addition and elimination) usually predominate for most systems. However, exceptions, such as methyl vinyl ketone, selectively give 1,4-addition products. This has been rationalized by DFT calculations that show that major conformational effects are involved, controlled mainly by steric effects of carbonyl substituents, resulting in a model that provides simple and predictable preparation of α,β- unsaturated imines for in situ utilization in synthesis.
Novel transformation of α,β-unsaturated aldehydes and ketones into γ-amino alcohols or 1,3-oxazines via a 4 or 5 step, one-pot sequence
Calow, Adam D. J.,Batsanov, Andrei S.,Fernández, Elena,Solé, Cristina,Whiting, Andrew
, p. 11401 - 11403 (2013/01/15)
An efficient, 4-step, one-pot, highly stereoselective route to γ-amino alcohols has been developed via an in situ α,β- unsaturated imine formation, β-boration, reduction (CN) and oxidation (C-B) sequence and especially for certain water-soluble γ-amino alcohols, a further step can be added to directly access the corresponding 1,3-oxazine derivatives.
The enantioselective synthesis of tetracyclic methyllycaconitine analogues
Sparrow, Kevin,Barker, David,Brimble, Margaret A.
experimental part, p. 7989 - 7999 (2011/11/07)
A new enantioselective synthesis of ABEF ring analogues of methyllycaconitine has been developed using a chiral cobalt(III) salen-catalyzed Diels-Alder reaction to form the B ring. Subsequent elaboration to form the A, E and F rings was achieved by sequential Dieckmann, Mannich and Wacker-type cyclizations to afford tetracyclic analogues in 97.5% ee.
Asymmetric addition of trimethylsilylcyanide to N-benzylimines catalyzed by recyclable chiral dimeric V(V) salen complex
Khan, Noor-ul H.,Saravanan,Kureshy, Rukhsana I.,Abdi, Sayed H.R.,Sadhukhan, Arghya,Bajaj, Hari C.
experimental part, p. 1133 - 1137 (2010/06/13)
Chiral dimeric vanadium (V) salen complex (10 mol%) derived from 5,5-Methylene di-[(S,S)-{N-(3-tert-butyl salicylidine)-N′-(3′,5′-di-tert-butyl salicylidene)]-1,2-cyclohexanediamine] with vanadyl suphate followed by auto oxidation was used as efficient catalyst for enantioselective Strecker reaction of N-benzylimines with TMSCN at -30 °C. Excellent yield (92%) of α-aminonitrile and high chiral induction was achieved (ee up to 94%) in case of 2-methoxy substituted N-benzylimines in 10 h. The catalytic system worked well up to four cycles with retention of enantioselectivity.
