Literature DB >> 19007175

Tandem silylformylation-crotylsilylation/Tamao oxidation of internal alkynes: a remarkable example of generating complexity from simplicity.

Jared T Spletstoser1, Michael J Zacuto, James L Leighton.   

Abstract

The rhodium-catalyzed tandem silylformylation-crotylsilylation reaction has been extended to include internal alkynes. Tamao oxidation of the initial product leads to the production of a substituted enol, which undergoes highly diastereoselective tautomerization. The resulting one-pot procedure fashions three new stereocenters, a ketone, and a terminal alkene from a butenyl group, a propynyl group, a silyl hydride, H2O2, and CO.

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Year:  2008        PMID： 19007175      PMCID： PMC2628290          DOI： 10.1021/ol802489w

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  13 in total

1.  Tandem Intramolecular Alkyne Silylformylation-Allylsilylation: A Case of Remote 1,5-Asymmetric Induction Financial support was provided by the National Institutes of Health (National Institute of General Medical Sciences, GM58133). We are grateful to Bristol-Myers Squibb for generous financial support in the form of an Unrestricted Grant in Synthetic Organic Chemistry to J.L.L. We thank Merck Research Laboratories and DuPont Pharmaceuticals for generous financial support.

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8.  Griseochelin, a novel carboxylic acid antibiotic from Streptomyces griseus.

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Journal:  J Org Chem       Date:  2004-07-09       Impact factor: 4.354
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  13 in total

1.  Silylation reactions on nanoporous gold via homolytic Si-H activation of silanes.

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Journal:  Chem Sci       Date:  2018-04-30       Impact factor: 9.825

2.  Chemoselective Alteration of Fluorophore Scaffolds as a Strategy for the Development of Ratiometric Chemodosimeters.

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5.  Synthesis and Evaluation of a Linkable Functional Group-Equipped Analogue of the Epothilones.

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Journal:  Chem Sci       Date:  2013-04-01       Impact factor: 9.825

7.  Complex fragment coupling by crotylation: A powerful tool for polyketide natural product synthesis.

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8.  A Highly Stereoselective, Efficient, and Scalable Synthesis of the C(1)-C(9) Fragment of the Epothilones.

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9.  A highly step-economical synthesis of dictyostatin.

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10.  An "aprotic" Tamao oxidation/syn-selective tautomerization reaction for the efficient synthesis of the C1-C9 fragment of fludelone.

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