Literature DB >> 16930080

Mechanism of acylation of lithium phenylacetylide with a Weinreb amide.

Bo Qu1, David B Collum.   

Abstract

Additions of lithium phenylacetylide to a Weinreb amide are described. Dimeric lithium acetylide reacts via a monosolvated monomer-based transition structure. The robust tetrahedral intermediate forms sequentially a C(1) 2:2 mixed tetramer with the excess lithium acetylide and a 1:3 (alkoxide-rich) mixed tetramer. The stabilities of the mixed tetramers are consistent with a pronounced autoinhibition.

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Year:  2006        PMID: 16930080     DOI: 10.1021/jo061223w

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


  4 in total

1.  Lithium Enolates Derived from Weinreb Amides: Insights into Five-Membered Chelate Rings.

Authors:  Michael J Houghton; David B Collum
Journal:  J Org Chem       Date:  2016-10-17       Impact factor: 4.354

2.  Synthesis of chirally pure 1-deoxy-d-xylulose-5-phosphate : A substrate for IspC assay to determine M. tb inhibitor.

Authors:  Benson J Edagwa; Prabagaran Narayanasamy
Journal:  Chem Sci J       Date:  2013-12-30

3.  β-Amino functionalization of cinnamic Weinreb amides in ionic liquid.

Authors:  Yi-Ning Wang; Guo-Xiang Sun; Gang Qi
Journal:  Beilstein J Org Chem       Date:  2016-11-11       Impact factor: 2.883

4.  Synthesis of HDAC Substrate Peptidomimetic Inhibitors Using Fmoc Amino Acids Incorporating Zinc-Binding Groups.

Authors:  Amit Mahindra; Christopher J Millard; Iona Black; Lewis J Archibald; John W R Schwabe; Andrew G Jamieson
Journal:  Org Lett       Date:  2019-04-18       Impact factor: 6.005

  4 in total

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