Diastereoselectivity in the Staudinger reaction: a useful probe for investigation of nonthermal microwave effects

Libo Hu; Yikai Wang; Bonan Li; Da Ming Du; Jiaxi Xu

doi:10.1016/j.tet.2007.06.112

Diastereoselectivity in the Staudinger reaction: a useful probe for investigation of nonthermal microwave effects

Libo Hu, Yikai Wang, Bonan Li, Da Ming Du, Jiaxi Xu^*

^*Corresponding author for this work

Peking University

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

48 Citations (Scopus)

Abstract

The effect of microwave irradiation on the selectivity, especially stereoselectivity, is one of the most important issues in microwave-assisted organic reactions. The diastereoselectivity in Staudinger reactions involving the representative ketenes and the corresponding matched imines has been used as a probe to investigate carefully the existence of the specific nonthermal microwave effects. The results indicate that the microwave irradiation-controlled stereoselectivity in the Staudinger reaction is in fact the contribution of temperature. No specific nonthermal microwave effect was found in the Staudinger reaction.

Original language	English
Pages (from-to)	9387-9392
Number of pages	6
Journal	Tetrahedron
Volume	63
Issue number	38
DOIs	https://doi.org/10.1016/j.tet.2007.06.112
Publication status	Published - 17 Sept 2007
Externally published	Yes

Keywords

Diastereoselectivity
Imine
Ketene
Microwave
Nonthermal effect
Staudinger reaction
Stereoselectivity
Temperature
β-Lactam

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10.1016/j.tet.2007.06.112

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title = "Diastereoselectivity in the Staudinger reaction: a useful probe for investigation of nonthermal microwave effects",

abstract = "The effect of microwave irradiation on the selectivity, especially stereoselectivity, is one of the most important issues in microwave-assisted organic reactions. The diastereoselectivity in Staudinger reactions involving the representative ketenes and the corresponding matched imines has been used as a probe to investigate carefully the existence of the specific nonthermal microwave effects. The results indicate that the microwave irradiation-controlled stereoselectivity in the Staudinger reaction is in fact the contribution of temperature. No specific nonthermal microwave effect was found in the Staudinger reaction.",

keywords = "Diastereoselectivity, Imine, Ketene, Microwave, Nonthermal effect, Staudinger reaction, Stereoselectivity, Temperature, β-Lactam",

author = "Libo Hu and Yikai Wang and Bonan Li and Du, \{Da Ming\} and Jiaxi Xu",

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T1 - Diastereoselectivity in the Staudinger reaction

T2 - a useful probe for investigation of nonthermal microwave effects

AU - Hu, Libo

AU - Wang, Yikai

AU - Li, Bonan

AU - Du, Da Ming

AU - Xu, Jiaxi

PY - 2007/9/17

Y1 - 2007/9/17

N2 - The effect of microwave irradiation on the selectivity, especially stereoselectivity, is one of the most important issues in microwave-assisted organic reactions. The diastereoselectivity in Staudinger reactions involving the representative ketenes and the corresponding matched imines has been used as a probe to investigate carefully the existence of the specific nonthermal microwave effects. The results indicate that the microwave irradiation-controlled stereoselectivity in the Staudinger reaction is in fact the contribution of temperature. No specific nonthermal microwave effect was found in the Staudinger reaction.

AB - The effect of microwave irradiation on the selectivity, especially stereoselectivity, is one of the most important issues in microwave-assisted organic reactions. The diastereoselectivity in Staudinger reactions involving the representative ketenes and the corresponding matched imines has been used as a probe to investigate carefully the existence of the specific nonthermal microwave effects. The results indicate that the microwave irradiation-controlled stereoselectivity in the Staudinger reaction is in fact the contribution of temperature. No specific nonthermal microwave effect was found in the Staudinger reaction.

KW - Diastereoselectivity

KW - Imine

KW - Ketene

KW - Microwave

KW - Nonthermal effect

KW - Staudinger reaction

KW - Stereoselectivity

KW - Temperature

KW - β-Lactam

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DO - 10.1016/j.tet.2007.06.112

M3 - Article

AN - SCOPUS:34547691274

SN - 0040-4020

VL - 63

SP - 9387

EP - 9392

JO - Tetrahedron

JF - Tetrahedron

IS - 38

ER -

Diastereoselectivity in the Staudinger reaction: a useful probe for investigation of nonthermal microwave effects

Abstract

Keywords

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