Stereoselective reactions with imines

Dai, Li‐Xin; Yang, Lin; Hou, Xue‐Long; Zhou, Yuhan

doi:10.1351/pac199971061033

Cited by 27 publications

(16 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The cluster-bound imine substrate is putatively activated for further chemical transformations, [21] of which, the application of such complexes toward chemically and biologically significant N-containing compounds, are of particular interest. [22] Adding further interest to the synthetic use of these complexes is the ability to execute multiple-site reactions and the potential of developing highly efficient catalytic schemes. Research in these directions is being pursued.…”

Section: A Series Of Imino Complexes Of the [Re 6 A C H T U N G T R Ementioning

confidence: 99%

Geometrically Specific Imino Complexes of the [Re₆(μ₃‐Se)₈]²⁺ Core‐Containing Clusters

Trương

Alster

et al. 2010

Chemistry A European J

View full text Add to dashboard Cite

The reactions of nitrile complexes of the [Re(6)(μ(3)-Se)(8)](2+) core-containing clusters, [Re(6)(μ(3)-Se)(8)(PEt(3))(n)(CH(3)CN)(6-n)](2+) [n = 5 (1); n = 4, cis- (2) and trans- (3); n = 0 (4)], with organic azides C(6)H(5)CH(CH(3))N(3) and C(6)H(5)CH(2)N(3) produced the corresponding cationic imino complexes of the general formula [Re(6)(μ(3)-Se)(8)(PEt(3))(n)(L)(6-n)](2+) [L = PhN=CHCH(3): n = 5 (5); n = 4, cis- (6) and trans- (7); n = 0 (8) and L = HN=CHPh: n = 5 (9); n = 4, cis- (10) and trans- (11)]. These novel complexes were characterized by NMR spectroscopy ((1)H and (31)P) and single-crystal X-ray diffraction. A mechanism involving the migration of one of the groups on the azido α-C atom to the α-N atom of the azido complex, concerted with the photo-expulsion of N(2), was invoked to rationalize the formation of the imino complexes. Density functional theory (DFT) calculations indicated that due to the coordination with and activation by the cluster core, the energy of the electronic transition responsible for the photo-decomposition of a cluster-bound azide is much reduced with respect to its pure organic counterpart. The observed geometric specificity was rationalized by using the calculated and optimized preferred ground-state conformation of the cluster-azido intermediates.

show abstract

Section: A Series Of Imino Complexes Of the [Re 6 A C H T U N G T R Ementioning

confidence: 99%

Geometrically Specific Imino Complexes of the [Re₆(μ₃‐Se)₈]²⁺ Core‐Containing Clusters

Trương

Alster

et al. 2010

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…After selective reduction of nitrobenzene 1 , the resulting aniline 4 undergoes condensation with aldehyde 2 to the corresponding imine or iminium ion. They likely adopt the E ‐configuration, because E ‐imines and E ‐iminium salts are known to be more stable than the corresponding Z ‐isomers . The formation of the C=N double bond is followed by an intramolecular aza‐Diels–Alder reaction that yields the trans–trans diastereomer with an equatorial phenyl group at C‐7 (Figure ) exclusively.…”

Section: Resultsmentioning

confidence: 99%

The First Domino Reduction/Imine Formation/Intramolecular Aza‐Diels–Alder Reaction for the Diastereoselective Preparation of Tetrahydrochromano[4,3‐b]quinolines

2016

View full text Add to dashboard Cite

The first domino reduction/imine formation/intramolecular aza‐Diels–Alder reaction is reported. Tetrahydrochromano[4,3‐b]quinolines are formed with high exo‐E‐anti selectivity and yields up to 87 % when a nitrobenzene and a 2‐(cinnamyloxy)benzaldehyde are reacted in aqueous citric acid by using iron as a reductant and montmorillonite K10 as a catalyst. The domino process starts with the in situ reduction of the nitrobenzene to the corresponding aniline, which is followed by imine formation and terminated by an intramolecular aza‐Diels–Alder reaction.

show abstract

“…Consequently, (E) and (Z) oxaziridines may be formed from (anti)-imines according to a concerted mechanism (Scheme 3). (ii) The low reactivity of N-alkylimines toward nucleophiles is well-known [32]. It is improved by the presence of electronwithdrawing nitrogen substituents (RSO 2 and Ph 2 P(O)).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of oxaziridines by oxidation of imines with the trichloroacetonitrile–hydrogen peroxide system

Kraı̈em

Othman

Hassine

2004

Comptes Rendus. Chimie

View full text Add to dashboard Cite

Stereoselective reactions with imines

Cited by 27 publications

References 16 publications

Geometrically Specific Imino Complexes of the [Re₆(μ₃‐Se)₈]²⁺ Core‐Containing Clusters

Geometrically Specific Imino Complexes of the [Re₆(μ₃‐Se)₈]²⁺ Core‐Containing Clusters

The First Domino Reduction/Imine Formation/Intramolecular Aza‐Diels–Alder Reaction for the Diastereoselective Preparation of Tetrahydrochromano[4,3‐b]quinolines

Synthesis of oxaziridines by oxidation of imines with the trichloroacetonitrile–hydrogen peroxide system

Contact Info

Product

Resources

About

Stereoselective reactions with imines

Cited by 27 publications

References 16 publications

Geometrically Specific Imino Complexes of the [Re6(μ3‐Se)8]2+ Core‐Containing Clusters

Geometrically Specific Imino Complexes of the [Re6(μ3‐Se)8]2+ Core‐Containing Clusters

The First Domino Reduction/Imine Formation/Intramolecular Aza‐Diels–Alder Reaction for the Diastereoselective Preparation of Tetrahydrochromano[4,3‐b]quinolines

Synthesis of oxaziridines by oxidation of imines with the trichloroacetonitrile–hydrogen peroxide system

Contact Info

Product

Resources

About

Geometrically Specific Imino Complexes of the [Re₆(μ₃‐Se)₈]²⁺ Core‐Containing Clusters

Geometrically Specific Imino Complexes of the [Re₆(μ₃‐Se)₈]²⁺ Core‐Containing Clusters