Synthesis of morpholin-2-ones by chemoselective intramolecular rhodium-catalyzed reductive ring expansion of oxazolidines

Organic Letters

Volumn 10, Issue 7, 2008, Pages 1357-1359

  Vasylyev, Maksym ^a   Alper, Howard ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

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EID: 59849125865     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol703135w     Document Type: Article

References (25)

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24. The fact that only 63% of the compound has N-CH2D structural fragment (calculated according to the integral values of the NMR spectrum, (S11 (inset), Supporting Information) may be due to hydrogen-deuterium exchange which occurs in rhodium hydride bonded to 1,5-cyclooctadiene.
25. 2 were dissolved in 10 mL of anhydrous toluene in a glass liner equipped with a magnetic stirring bar. To this solution was added 0.1 mmol of KI, and the liner was inserted into a 45 mL autoclave, which was then sealed. Carbon monoxide, 5 atm, was introduced to the autoclave by the two consecutive pump-release cycles. Finally, hydrogen gas was introduced into the autoclave bringing the overall pressure to 10 atm. The autoclave was placed in a thermostated oil bath at 100 °C and the reaction was carried out for 15 h. The autoclave was then cooled, and pressure was released. The reaction mixture was concentrated, and the residue was subjected to flash chromatography.