Highly enantioselective synthesis of (E)-allylic alcohols

Hsyueh Liang Wu; Ping Yu Wu; Biing Jiun Uang

doi:10.1021/jo0709403

Highly enantioselective synthesis of (E)-allylic alcohols

Hsyueh Liang Wu, Ping Yu Wu, Biing Jiun Uang^*

^*Corresponding author for this work

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

28 Citations (Scopus)

Abstract

(Chemical Equation Presented) The asymmetric addition of alkenylzincs to aromatic and a-branched aliphatic aldehydes catalyzed by 1 generated the corresponding (E)-allylic alcohols with >95% ee and good to excellent chemical yields, especially >99.5% ee was observed in the case of 4-CF ₃-benzaldehyde. Notably, 1 is an effective ligand to catalyze the addition of disubstituted (R₂ = R₃ = ethyl) and bulky substituted (R₂ - H, R₃ = tert-butyl) alkenylzincs to benzaldehyde, affording the corresponding allylic alcohols both with 96% ee.

Original language	English
Pages (from-to)	5935-5937
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	72
Issue number	15
DOIs	https://doi.org/10.1021/jo0709403
Publication status	Published - 2007 Jul 20
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "Highly enantioselective synthesis of (E)-allylic alcohols",

abstract = "(Chemical Equation Presented) The asymmetric addition of alkenylzincs to aromatic and a-branched aliphatic aldehydes catalyzed by 1 generated the corresponding (E)-allylic alcohols with >95% ee and good to excellent chemical yields, especially >99.5% ee was observed in the case of 4-CF 3-benzaldehyde. Notably, 1 is an effective ligand to catalyze the addition of disubstituted (R2 = R3 = ethyl) and bulky substituted (R2 - H, R3 = tert-butyl) alkenylzincs to benzaldehyde, affording the corresponding allylic alcohols both with 96% ee.",

author = "Wu, {Hsyueh Liang} and Wu, {Ping Yu} and Uang, {Biing Jiun}",

year = "2007",

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doi = "10.1021/jo0709403",

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journal = "Journal of Organic Chemistry",

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T1 - Highly enantioselective synthesis of (E)-allylic alcohols

AU - Wu, Hsyueh Liang

AU - Wu, Ping Yu

AU - Uang, Biing Jiun

PY - 2007/7/20

Y1 - 2007/7/20

N2 - (Chemical Equation Presented) The asymmetric addition of alkenylzincs to aromatic and a-branched aliphatic aldehydes catalyzed by 1 generated the corresponding (E)-allylic alcohols with >95% ee and good to excellent chemical yields, especially >99.5% ee was observed in the case of 4-CF 3-benzaldehyde. Notably, 1 is an effective ligand to catalyze the addition of disubstituted (R2 = R3 = ethyl) and bulky substituted (R2 - H, R3 = tert-butyl) alkenylzincs to benzaldehyde, affording the corresponding allylic alcohols both with 96% ee.

AB - (Chemical Equation Presented) The asymmetric addition of alkenylzincs to aromatic and a-branched aliphatic aldehydes catalyzed by 1 generated the corresponding (E)-allylic alcohols with >95% ee and good to excellent chemical yields, especially >99.5% ee was observed in the case of 4-CF 3-benzaldehyde. Notably, 1 is an effective ligand to catalyze the addition of disubstituted (R2 = R3 = ethyl) and bulky substituted (R2 - H, R3 = tert-butyl) alkenylzincs to benzaldehyde, affording the corresponding allylic alcohols both with 96% ee.

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JF - Journal of Organic Chemistry

IS - 15

ER -

Highly enantioselective synthesis of (E)-allylic alcohols

Abstract

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