533902-67-9Relevant academic research and scientific papers
Triphosgene-amine base promoted chlorination of unactivated aliphatic alcohols
Villalpando, Andres,Ayala, Caitlan E.,Watson, Christopher B.,Kartika, Rendy
, p. 3989 - 3996 (2013/06/04)
Unactivated α-branched primary and secondary aliphatic alcohols have been successfully transformed into their corresponding alkyl chlorides in high yields upon treatment with a mixture of triphosgene and pyridine in dichloromethane at reflux. These mild chlorination conditions are high yielding, stereospecific, and well tolerated by numerous sensitive functionalities. Furthermore, no nuisance waste products are generated in the course of the reactions.
An oxidative entry into the amido trioxadecalin ring system.
Rech, Jason C,Floreancig, Paul E
, p. 1495 - 1498 (2007/10/03)
The amido trioxadecalin ring system is a key structural component of the architecturally interesting anticancer and immunosuppressive agents of the mycalamide, theopederin, and onnamide families of natural products. We report a new entry into this structure in which a mixed acetal serves as a surrogate for a formaldehyde hemiacetal in an addition to an oxidatively generated acyliminium ion. The stereochemical outcome of this process can be explained by the conformational preferences of the product ring system. [reaction: see text]
