Question

I l Professor David Evans of Harvard (Prof. Schee cheerer's Ph.D. advisor) developed versatile compounds called oxazolidinones as "chiral auxiliarie willaries" for organic synthesis. To access these, alinol) and carbonyl compounds (e.g., one can react reduced forms of amino acids (e.g., valin diethylcarbonate) as shown below. yicarbonate) as shown below. Write a mechanism for the formation of the Oxazolidinone. NH2 0 Y OH = ΕΙΟ ΟΕΙ (R)-valinol diethyl- carbonate oxazolidinone

Answer 1

The complete curved arrow mechanism for Oxazolidinone is given below.

O NH2 0H HN & Eto OET Mechanism: tot NE+ OH "Eto OE+ сон OET AOER -OEt) HN GOET он -OH OE HN-TOET @gm OF HN