Walt aquired most of his chemistry knowledge by reading journal articles. Here are a few of his favorites:

 

 

 

 

 

 

 

 

 

Our Paper's Source:

Phillips, A. J.; Uto, Y.; Wipf, P.; Reno, M. J; Williams, D. R. Org. Lett. 2000, 2 (8), 1165-1168.

This article investigates the usage of diethylaminosulfur trifluoride (DAST) as a means to convert β-hydroxy amides to oxazolines at low temperature through cyclodehydration. DAST was used in slight excess in addition to K2CO3 which resulted in the smoothy cyclization to oxazolines. It is also included that there are some limitations within the method of using DAST which can be contributed to unfavorable electronic contributions of groups such as adjacent methyl esters. It was discovered that the reaction could be done in a one-pot process because of its rapid cyclization at low temperatures. Furthermore, it can be concluded that DAST and Deoxo-Fluor, a similar molecule to DAST, are useful reagents to synthesize oxazolines in which they are compatible with a wide variety of functional groups

Citing Sources

Oberheide, A.; Pflanze, S.; Stallforth, P.; Arndt, H. Org. Lett. 2019, 21 (3), 729-732.

This article shows the transformation of an amide to an oxazoline using DAST with the loss of oxygen.

 

Schrof, R.; Altmann, K. Org. Lett. 2018, 20 (23), 7679-7683.

This article shows the transformation of a hydroxy amide to an oxazoline using DAST with the loss of iodine.

Oguma, T.; Anan, K.; Suzuki, S.; Hisakawa, S.; Takada, A.; Ogawa, M.; Kusakabe, K. J. Org. Chem. 2018 .

DOI: 10.1021/acs.joc.8b02179

This article shows the transformation of product 6 to a 1,3-thiazine due to an intramolecular cyclization using DAST.