Novel approach to multifunctionalized homoallylic alcohols via regioselective ring opening of aryl oxiranes with 3-iodo allenoates.
[reaction: see text] 3-Iodo allenoates were generated in situ and utilized, for the first time, in the ring opening of oxiranes in a regioselective fashion. This simple one-pot three-component reaction protocol provides easy access to highly functionalized homoallylic alcohols in good yields and moderate to very good (Z/E) selectivity. The two functional groups (ester and halogen) can be further subjected to many synthetic transformations.
Kattuboina
Adiseshu
A
Department of Chemistry & Biochemistry, Texas Tech University, Lubbock, 79409-1061, USA.
Kaur
Parminder
P
Timmons
Cody
C
Li
Guigen
G
D000438:Alcohols / Q000138:chemical synthesis*; D020650:Combinatorial Chemistry Techniques; D005027:Ethylene Oxide / Q000737:chemistry*; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000438:Alcohols; D006847:Hydrocarbons, Iodinated; D005027:Ethylene Oxide