Metal-Free Cycloetherification by in Situ Generated P-Stereogenic -Diazanium Intermediates: A Convergent Synthesis of Enantiomerically Pure Dihydrobenzooxaphospholes.

abstract

• A metal-free tandem reaction, initiated by the generation of a diazonium cation and followed by cycloetherification, was developed. Acid-promoted de-tert-butylation of N-nitroso N-tert-butylamine was used to generate a diazonium cation in situ, demonstrating a new application of nitroso chemistry. This reaction was employed in the synthesis of substituted benzofuran-3(2H)-ones and dihydrobenzo[d][1,3]oxaphosphole 3-oxides.

authors

• Kurouski, Dzmitry

published proceedings

• Org Lett

author list (cited authors)

• Li, S., Han, Z. S., Viereck, P., Lee, H., Kurouski, D., Senanayake, C. H., & Tsantrizos, Y. S.

citation count

• 4

complete list of authors

• Li, Shi-Guang||Han, Zhengxu S||Viereck, Peter||Lee, Heewon||Kurouski, Dmitry||Senanayake, Chris H||Tsantrizos, Youla S

publication date

• February 2017

publisher

• American Chemical Society (ACS)  Publisher

published in

• Organic Letters  Journal

keywords

• 0302 Inorganic Chemistry
• 0305 Organic Chemistry

PubMed Central ID

• 28155279

Digital Object Identifier (DOI)

• 10.1021/acs.orglett.7b00051

start page

• 894

end page

• 897

volume

• 19

issue

• 4

URL

• http://dx.doi.org/10.1021/acs.orglett.7b00051