(Cyanomethylene)phosphoranes as Novel Carbonyl 1,1-Dipole Synthons: An Efficient Synthesis of .alpha.-Keto Acids, Esters, and Amides

Harry H. Wasserman; Wen-Bin Ho

doi:10.1021/jo00095a005

(Cyanomethylene)phosphoranes as Novel Carbonyl 1,1-Dipole Synthons: An Efficient Synthesis of .alpha.-Keto Acids, Esters, and Amides

The Journal of Organic Chemistry ◽

10.1021/jo00095a005 ◽

1994 ◽

Vol 59 (16) ◽

pp. 4364-4366 ◽

Cited By ~ 85

Author(s):

Harry H. Wasserman ◽

Wen-Bin Ho

Keyword(s):

Efficient Synthesis ◽

Keto Acids

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Open Gate of Corynebacterium glutamicum Threonine Deaminase for Efficient Synthesis of Bulky α-Keto Acids

ACS Catalysis ◽

10.1021/acscatal.0c01672 ◽

2020 ◽

Vol 10 (17) ◽

pp. 9994-10004

Author(s):

Wei Song ◽

Xin Xu ◽

Cong Gao ◽

Yuxuan Zhang ◽

Jing Wu ◽

...

Keyword(s):

Corynebacterium Glutamicum ◽

Efficient Synthesis ◽

Threonine Deaminase ◽

Keto Acids

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Sustainable synthesis of 3-substituted phthalides via a catalytic one-pot cascade strategy from 2-formylbenzoic acid with β-keto acids in glycerol

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.13.139 ◽

2017 ◽

Vol 13 ◽

pp. 1425-1429 ◽

Cited By ~ 1

Author(s):

Lina Jia ◽

Fuzhong Han

Keyword(s):

Natural Products ◽

Cascade Reaction ◽

Catalytic Process ◽

Efficient Synthesis ◽

One Pot ◽

Keto Acids ◽

Synthesis Strategy ◽

Therapeutic Activities

Background: Phthalides are privileged constituents of numerous pharmaceuticals, natural products and agrochemicals and exhibit several biological and therapeutic activities. Therefore, the development of new, facile, and sustainable strategies for the construction of these moieties is highly desired. Results: A broad substrate scope for β-keto acids was found to be strongly compatible with this catalytic process, affording a wide variety of 3-substituted phthalides in good to excellent yields. Conclusion: A concise and efficient synthesis strategy of 3-substituted phthalides from 2-formylbenzoic acid and β-keto acids via a catalytic one-pot cascade reaction in glycerol has been accomplished.

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Radical Carbonylative Synthesis of Heterocycles by Visible Light Photoredox Catalysis

Catalysts ◽

10.3390/catal10091054 ◽

2020 ◽

Vol 10 (9) ◽

pp. 1054

Author(s):

Xiao-Qiang Hu ◽

Zi-Kui Liu ◽

Wen-Jing Xiao

Keyword(s):

Visible Light ◽

Efficient Synthesis ◽

Acyl Radical ◽

Acyl Chlorides ◽

Aryl Radicals ◽

Keto Acids ◽

Acyl Radicals ◽

Different Types ◽

The Impact ◽

Visible Light Photocatalytic

Visible light photocatalytic radical carbonylation has been established as a robust tool for the efficient synthesis of carbonyl-containing compounds. Acyl radicals serve as the key intermediates in these useful transformations and can be generated from the addition of alkyl or aryl radicals to carbon monoxide (CO) or various acyl radical precursors such as aldehydes, carboxylic acids, anhydrides, acyl chlorides or α-keto acids. In this review, we aim to summarize the impact of visible light-induced acyl radical carbonylation reactions on the synthesis of oxygen and nitrogen heterocycles. The discussion is mainly categorized based on different types of acyl radical precursors.

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