3- Iodopropionic acid, reaction with

The reaction of 5-iodopropionic acid has been studied and its biological implications discussed. "... 

Preparative Methods is prepared by reaction of 2-aminopyridine with either Ac/yZic acid itself or an equivalent (2-bromo- or 2-iodopropionic acid, Methyl Acrylate, ethyl 2-bromopropionate, P-Propiolactone). ... 

A new synthesis of ( )-menthofuran (155) has been described which involves a three-step reaction sequence from the cyclohexanone (152) via direct C-alkylation with ethyl 2-iodopropionate to give (153) (Scheme 35). Hydrolysis of the diester (153) with hydrochloric acid afforded 3,6-dimethyl-2,4,5,6,7,7a-hexahydrobenzofuran-2-one (154). The final step in the sequence was the conversion of the a,/3-unsaturated y-lactone ring into the furan ring by reduction with lithium aluminum hydride and 2-propanol to afford (i)-menthofuran (155) in satisfactory yield (80JOC1517). 

The combination of aluminum Lewis acids and chiral diols has allowed for modest enantioselectivities in similar reactions using oxazolidinone templates and a-iodopropionate substrate as in Eq. (13.30) [42]. The 4,4-dimethyl substituent on the oxazolidinone (99) favors the s-cis conformation for the intermediate radical. Enantioselectivities of 32 and 34% and yields above 90% were obtained for ally-lations with R=H and R=Me respectively. 

---