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Literature DB >> 11671493

Highly Selective Synthesis of Z-Unsaturated Esters by Using New Horner-Emmons Reagents, Ethyl (Diarylphosphono)acetates.

Abstract

New Horner-Emmons reagents, ethyl (diarylphosphono)acetates 1, were prepared from triethyl phosphonoacetate, PCl(5), and the corresponding phenols. The reaction of 1 with several kinds of aldehydes in the presence of Triton B or NaH in THF solvent revealed that these reagents are useful for the synthesis of Z-unsaturated esters. Among the reagents examined, ethyl(di-o-tolylphosphono)-, [bis(o-ethylphenyl)phosphono]-, and [bis(o-isopropylphenyl)phosphono]acetates (1k-m) were found to be the most effective, giving Z-unsaturated esters with 93-99% selectivity.

Entities: Chemical

Year: 1997 PMID： 11671493 DOI： 10.1021/jo970057c

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

15 in total

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Authors: Janice M H Cheng; Ligong Liu; Daniel G Pellicci; Scott J J Reddiex; Rachel N Cotton; Tan-Yun Cheng; David C Young; Ildiko Van Rhijn; D Branch Moody; Jamie Rossjohn; David P Fairlie; Dale I Godfrey; Spencer J Williams
Journal: Chemistry Date: 2017-01-18 Impact factor: 5.236

Highly Selective Synthesis of Z-Unsaturated Esters by Using New Horner-Emmons Reagents, Ethyl (Diarylphosphono)acetates.

Review 1. Synthetic Strategies Employed for the Construction of Fostriecin and Related Natural Products.

2. Total Synthesis of Mycobacterium tuberculosis Dideoxymycobactin-838 and Stereoisomers: Diverse CD1a-Restricted T Cells Display a Common Hierarchy of Lipopeptide Recognition.

Review 3. Challenges and discoveries in the total synthesis of complex polyketide natural products.

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