Asymmetric boron conjugate addition to α,β-unsaturated carbonyl compounds catalyzed by CuOTf/Josiphos under non-alkaline conditions

Jian Bo Xie; Siqi Lin; Jian Luo; Jianbin Wu; Timothy R. Winn; Guigen Li

doi:10.1039/c4qo00271g

Asymmetric boron conjugate addition to α,β-unsaturated carbonyl compounds catalyzed by CuOTf/Josiphos under non-alkaline conditions

Jian Bo Xie, Siqi Lin, Jian Luo, Jianbin Wu, Timothy R. Winn, Guigen Li

Chemistry and Biochemistry

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

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Abstract

The asymmetric boron conjugate addition onto α,β-unsaturated ketones and esters has been developed by using the CuOTf/Josiphos complex as the catalyst under non-alkaline conditions. It was found that the addition of MeOH into the reaction system is crucial to the catalytic reactivity. Good to excellent enantioselectivity (up to 96% ee) and yields (up to 98%) have been achieved for 15 examples.

Original language	English
Pages (from-to)	42-46
Number of pages	5
Journal	Organic Chemistry Frontiers
Volume	2
Issue number	1
DOIs	https://doi.org/10.1039/c4qo00271g
State	Published - Jan 2015

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abstract = "The asymmetric boron conjugate addition onto α,β-unsaturated ketones and esters has been developed by using the CuOTf/Josiphos complex as the catalyst under non-alkaline conditions. It was found that the addition of MeOH into the reaction system is crucial to the catalytic reactivity. Good to excellent enantioselectivity (up to 96% ee) and yields (up to 98%) have been achieved for 15 examples.",

author = "Xie, {Jian Bo} and Siqi Lin and Jian Luo and Jianbin Wu and Winn, {Timothy R.} and Guigen Li",

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AU - Xie, Jian Bo

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AU - Wu, Jianbin

AU - Winn, Timothy R.

AU - Li, Guigen

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AB - The asymmetric boron conjugate addition onto α,β-unsaturated ketones and esters has been developed by using the CuOTf/Josiphos complex as the catalyst under non-alkaline conditions. It was found that the addition of MeOH into the reaction system is crucial to the catalytic reactivity. Good to excellent enantioselectivity (up to 96% ee) and yields (up to 98%) have been achieved for 15 examples.

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Asymmetric boron conjugate addition to α,β-unsaturated carbonyl compounds catalyzed by CuOTf/Josiphos under non-alkaline conditions

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