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

Adiseshu Kattuboina; Parminder Kaur; Cody Timmons; Guigen Li

doi:10.1021/ol060828b

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

Adiseshu Kattuboina, Parminder Kaur, Cody Timmons, Guigen Li

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	2771-2774
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	13
DOIs	https://doi.org/10.1021/ol060828b
State	Published - Jun 22 2006

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abstract = "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.",

author = "Adiseshu Kattuboina and Parminder Kaur and Cody Timmons and Guigen Li",

year = "2006",

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AU - Kattuboina, Adiseshu

AU - Kaur, Parminder

AU - Timmons, Cody

AU - Li, Guigen

PY - 2006/6/22

Y1 - 2006/6/22

N2 - 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.

AB - 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.

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DO - 10.1021/ol060828b

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

Abstract

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