Hydroxymethylation of α-substituted nitroacetates

Cong Bin Ji; Yun Lin Liu; Zhong Yan Cao; Yi Yu Zhang; Jian Zhou

doi:10.1016/j.tetlet.2011.09.020

Hydroxymethylation of α-substituted nitroacetates

Cong Bin Ji, Yun Lin Liu, Zhong Yan Cao, Yi Yu Zhang, Jian Zhou^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

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

36 Scopus citations

Abstract

Only 1 mol % of K₃PO₄ is efficient enough to catalyze the hydroxymethylation of α-substituted nitroacetates in good to excellent yield. Both aliphatic and aryl substituted nitroacetates work well under this reaction. The first catalytic asymmetric version of this reaction also reported that 10 mol % of cupreidine could catalyze this reaction up to 71% ee and 89% yield. Paraformaldehyde and formalin could both serve as the hydroxymethylation C1 unit. The synthetic application of products is also demonstrated.

Original language	English
Pages (from-to)	6118-6121
Number of pages	4
Journal	Tetrahedron Letters
Volume	52
Issue number	46
DOIs	https://doi.org/10.1016/j.tetlet.2011.09.020
State	Published - 16 Nov 2011

Keywords

Hydroxymethylation
Tetrasubstituted carbon
α-Substituted nitroacetates

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10.1016/j.tetlet.2011.09.020

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@article{f6e9108cbff940fc98ffaa831987fb26,

title = "Hydroxymethylation of α-substituted nitroacetates",

abstract = "Only 1 mol \% of K3PO4 is efficient enough to catalyze the hydroxymethylation of α-substituted nitroacetates in good to excellent yield. Both aliphatic and aryl substituted nitroacetates work well under this reaction. The first catalytic asymmetric version of this reaction also reported that 10 mol \% of cupreidine could catalyze this reaction up to 71\% ee and 89\% yield. Paraformaldehyde and formalin could both serve as the hydroxymethylation C1 unit. The synthetic application of products is also demonstrated.",

keywords = "Hydroxymethylation, Tetrasubstituted carbon, α-Substituted nitroacetates",

author = "Ji, \{Cong Bin\} and Liu, \{Yun Lin\} and Cao, \{Zhong Yan\} and Zhang, \{Yi Yu\} and Jian Zhou",

year = "2011",

month = nov,

day = "16",

doi = "10.1016/j.tetlet.2011.09.020",

language = "英语",

volume = "52",

pages = "6118--6121",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "46",

}

TY - JOUR

T1 - Hydroxymethylation of α-substituted nitroacetates

AU - Ji, Cong Bin

AU - Liu, Yun Lin

AU - Cao, Zhong Yan

AU - Zhang, Yi Yu

AU - Zhou, Jian

PY - 2011/11/16

Y1 - 2011/11/16

N2 - Only 1 mol % of K3PO4 is efficient enough to catalyze the hydroxymethylation of α-substituted nitroacetates in good to excellent yield. Both aliphatic and aryl substituted nitroacetates work well under this reaction. The first catalytic asymmetric version of this reaction also reported that 10 mol % of cupreidine could catalyze this reaction up to 71% ee and 89% yield. Paraformaldehyde and formalin could both serve as the hydroxymethylation C1 unit. The synthetic application of products is also demonstrated.

AB - Only 1 mol % of K3PO4 is efficient enough to catalyze the hydroxymethylation of α-substituted nitroacetates in good to excellent yield. Both aliphatic and aryl substituted nitroacetates work well under this reaction. The first catalytic asymmetric version of this reaction also reported that 10 mol % of cupreidine could catalyze this reaction up to 71% ee and 89% yield. Paraformaldehyde and formalin could both serve as the hydroxymethylation C1 unit. The synthetic application of products is also demonstrated.

KW - Hydroxymethylation

KW - Tetrasubstituted carbon

KW - α-Substituted nitroacetates

UR - https://www.scopus.com/pages/publications/80054101846

U2 - 10.1016/j.tetlet.2011.09.020

DO - 10.1016/j.tetlet.2011.09.020

M3 - 文章

AN - SCOPUS:80054101846

SN - 0040-4039

VL - 52

SP - 6118

EP - 6121

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 46

ER -

Hydroxymethylation of α-substituted nitroacetates

Abstract

Keywords

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