Synthesis, structure and reactivity of a macrocyclic imine: Aza-[13]-macrodiolides
The in situ synthesis and subsequent reactions of macrocylic imine 2 are reported. The imine was trapped with cyanotrimethylsilane to give α-amino nitrile aza-[13]-macrodiolides in a 1:1 ratio of diastereomers. A crystal structure of the syn α-cyano nitrile diastereomer, 7a, provided insights into the lack of selectivity in reactions of 2 relative to macrocyclic alkene 1. Reactions to functionalize the syn diastereomer 7a are also reported.
Ma, Jun,Vannam, Raghu,Terwilliger, Daniel W.,Peczuh, Mark W.
supporting information
p. 4255 - 4259
(2014/07/22)
Synthesis, structure and reactivity of a macrocyclic imine: Aza-[13]-macrodiolides
The in situ synthesis and subsequent reactions of macrocylic imine 2 are reported. The imine was trapped with cyanotrimethylsilane to give α-amino nitrile aza-[13]-macrodiolides in a 1:1 ratio of diastereomers. A crystal structure of the syn α-cyano nitrile diastereomer, 7a, provided insights into the lack of selectivity in reactions of 2 relative to macrocyclic alkene 1. Reactions to functionalize the syn diastereomer 7a are also reported.
Ma, Jun,Vannam, Raghu,Terwilliger, Daniel W.,Peczuh, Mark W.
supporting information
p. 4255 - 4259
(2016/11/19)
PHOTOCYCLISATION OF KETO-LACTAMS. A NEW SYNTHESIS OF FUNCTIONALIZED 1-AZA-BICYCLO(X.Y.0.)ALKANES
A series of 1-azabicyclo(x.y.0)alkanes has been synthesized using an intramolecular photoreduction.The methodology consists of a regioselective abstraction of a hydrogen α to the nitrogen of an amide by the triplet T1(n, ?*) of a carbonyl derivative.
Azzouzi, Assia,Dufour, Monique,Gramain, Jean-Claude,Remuson, Roland
p. 133 - 148
(2007/10/02)
Photo-oxidation of Oxazolidones and Hydantoins in the Presence of Benzophenone
Irradiation in the presence of benzophenone and oxygen of nitrogen-containing heterocycles having an NCO group yields products arising out of regioselective oxidation α to the nitrogen atom.Direct irradiation (in the absence of benzophenone and oxygen) of 5-methyl- and 5,5-dimethyl-hydantoins yields allophanates.The first step of this reaction involves the homolysis of the C(4) - C(5) bond of the hydantoin.
Gramain, Jean-Claude,Remuson, Roland
p. 2341 - 2346
(2007/10/02)
Synthesis in the diazasteroid group. XV. Syntheses of the 5,9- and 8,13-diazasteroids
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Takahata,Okajima,Yamazaki
p. 3632 - 3638
(2007/10/02)
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