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. 2011 Sep 16;13(18):4862-5.
doi: 10.1021/ol201947b. Epub 2011 Aug 17.

Introducing a new class of N-phosphoryl ynamides via Cu(I)-catalyzed amidations of alkynyl bromides

Kyle A DeKorver  1 , Mary C Walton, Troy D North, Richard P Hsung
Affiliations

Introducing a new class of N-phosphoryl ynamides via Cu(I)-catalyzed amidations of alkynyl bromides

Kyle A DeKorver et al. Org Lett. .

Abstract

We describe here the first synthesis of N-phosphoryl ynamides featuring C- and P-chirality via copper(I)-catalyzed amidative cross-couplings between phosphoramidates and phosphordiamidates with alkynyl bromides. Also featured is a tandem aza-Claisen-hetero-[2+2] cycloaddition for the synthesis of N-phosphoryl azetidin-2-imines.

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Figures

Figure 1
Figure 1
X-ray of Ynamide 15b.
Figure 2
Figure 2
X-rays of Diastereomeric Ynamides 17-eq and 17-ax.
Scheme 1
Scheme 1
Current Ynamide Electron-Withdrawing Groups.
Scheme 2
Scheme 2
Attempts at Ynamide Synthesis from Amino Alcohols.
Scheme 3
Scheme 3
Towards the Synthesis of N-Phosphoryl Azetidin-2-imines.
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References

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