Reactions of ethyl dichlorophosphate with MCl3 (M = Al, Cr) and UCl4

Karayannis, Nicholas M.; Pytlewski, L.L.; Mikulski, Chester M.

doi:10.1016/s0020-1693(00)90290-1

Cited by 38 publications

(62 citation statements)

References 29 publications

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“…This is consistent with a greater charge transfer (giving stronger bonding) from ligand to Zn in the Me3NO compound. It is consistent with the higher N--O bond polarity in the amine oxide (Linton, 1940;Karayannis, Pytlewski & Mikulski, 1973), and also with the spectrochemical evidence that tmno is a better donor than pyo (Drago, Donoghue & Herlocker, 1965). Over all the molecules (1)- (4) Herlocker (1969) that differences between the electronic spectra of [CoX2(Me3NO)2] complexes run as mulls and in solution are a result of five coordination through ligand bridging in the crystals.…”

Section: ) Crystals Of (2) Suitable For Diffractometry Were Obtasupporting

confidence: 83%

Structures of dichlorobis(trimethylamine oxide)cobalt(II), diiodobis(trimethylamine oxide)cobalt(II), dichlorobis(trimethylamine oxide)zinc and dibromobis(trimethylamine oxide)zinc

Jin¹,

Nieuwenhuyzen²,

Robinson³

et al. 1992

Acta Crystallogr C

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Section: ) Crystals Of (2) Suitable For Diffractometry Were Obtasupporting

confidence: 83%

Structures of dichlorobis(trimethylamine oxide)cobalt(II), diiodobis(trimethylamine oxide)cobalt(II), dichlorobis(trimethylamine oxide)zinc and dibromobis(trimethylamine oxide)zinc

Jin¹,

Nieuwenhuyzen²,

Robinson³

et al. 1992

Acta Crystallogr C

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“…[8] In this context, a great number of homochiral molecules containing amines, ethers, and phosphanes as electron-pair donors have been employed as asymmetric controllers in many enantioselective reactions. [9] It is well known that amine N-oxides possess a notable electron-pair donor property, which allows them to form different complexes with a variety of metal ions, [10] but few reports have dealt with the application of chiral N-oxides as chiral ligands [11] or as chiral promoters. [12] The axially chiral biquinoline N,NЈ-dioxide 2, one of the chiral N-oxides, attracted our attention because of its highly skewed chiral environment.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Strecker Reactions between Aldimines and Trimethylsilyl Cyanide Promoted by Chiral N,N′‐Dioxides

et al. 2003

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Axially chiral N,N′‐dioxide Lewis base promoters have been developed and have for the first time been applied to the asymmetric synthesis of α‐amino nitriles through cyanide addition to aldimines. The chiral 3,3′‐dimethyl‐2,2′‐biquinoline N,N′‐dioxide 2 exhibited high enantioselectivity for asymmetric Strecker reactions between N‐benzhydrylimines and trimethylsilyl cyanide. In the presence of 1 equiv. of chiral promoter 2, the cyanosilylation of aldimines afforded the corresponding α‐amino nitriles with ee values of up to 95%. Optically pure products (99% ee) were obtained simply by recrystallization in the cases of some of the products. Moreover, the promoter 2 could be recovered and reused at least four times without any loss of enantioselectivity and reactivity. A putative mechanism for the enantioselective Strecker reactions is also discussed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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“…BINOL derivatives have been successfully utilized as chirality inducers for highly stereoselective reactions because of their axial dissymmetry and molecular flexibility.6 We designed axially dissymmetric dioxides, 1, 1'-biisoquinoline N,N'-dioxide (1), which was patterned after BINOL, and 3, 3'-dimethy1-2,2'-biquinoline N, -dioxide (2), wherein the N-oxide moieties are embedded within a chiral pocket created by the walls of the biaryl unit ( Figure 1). Table 2.…”

Section: Design and Synthesis Of Chiral N-oxides5mentioning

confidence: 99%

Chiral N-Oxides as Catalysts or Ligands in Enantioselective Reactions

Nakajima

2003

J. Syn. Org. Chem., Jpn.

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: New enantioselective reactions catalyzed by chiral N-oxides or chiral N-oxide-metal complexes are discussed. Enantioselective allylations of aldehydes with allyltrichlorosilanes, aldol reactions with trichlorosilyl enol ethers, and epoxide-opening reactions with tetrachlorosilane were accomplished by using chiral bipyridine N,N'-dioxide derivatives as catalysts. In these reactions, hexacoordinate silicate intermediates played pivotal roles in the enantioselection. Furthermore, the N-oxides were efficient chiral ligands for the enantioselective conjugate addition of thiols catalyzed by cadmium complexes and Michael addition of

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Reactions of ethyl dichlorophosphate with MCl3 (M = Al, Cr) and UCl4

Cited by 38 publications

References 29 publications

Structures of dichlorobis(trimethylamine oxide)cobalt(II), diiodobis(trimethylamine oxide)cobalt(II), dichlorobis(trimethylamine oxide)zinc and dibromobis(trimethylamine oxide)zinc

Structures of dichlorobis(trimethylamine oxide)cobalt(II), diiodobis(trimethylamine oxide)cobalt(II), dichlorobis(trimethylamine oxide)zinc and dibromobis(trimethylamine oxide)zinc

Enantioselective Strecker Reactions between Aldimines and Trimethylsilyl Cyanide Promoted by Chiral N,N′‐Dioxides

Chiral N-Oxides as Catalysts or Ligands in Enantioselective Reactions

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