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Novel approach to multifunctionalized homoallylic alcohols via regioselective ring opening of aryl oxiranes with 3-iodo allenoates.


ABSTRACT: [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.

SUBMITTER: Kattuboina A 

PROVIDER: S-EPMC2613809 | biostudies-literature | 2006 Jun

REPOSITORIES: biostudies-literature

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Novel approach to multifunctionalized homoallylic alcohols via regioselective ring opening of aryl oxiranes with 3-iodo allenoates.

Kattuboina Adiseshu A   Kaur Parminder P   Timmons Cody C   Li Guigen G  

Organic letters 20060601 13


[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. ...[more]

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