Multi-component reactions allow for the generation of complex molecular scaffolds in a single synthetic operation from simple building blocks.1 In this context, the Petasis 3-component reaction is particularly useful for the synthesis of anti-amino alcohols from amines, a-hydroxy aldehydes and boronic acids. We now wish to report a variant of this powerful reaction, where hydrazides 1 ,2 a-hydroxy aldehydes 2 and two boronic acids, typically an electron-rich boronic acid 3 and an electron-poor boronic acid 4 , are combined to give novel boron heterocyclic compounds 6 . This 4-component reaction is highly modular and proceeds with excellent diastereoselectivity, providing the desired products 6 in high yields. In recent years there has been profound interest in boron heterocycles, e.g. as protecting groups3 and organocatalysts,4 and we foresee many exciting applications of these scaffolds in the future. Figure 1. <img src='https://acs-archive-assets2.s3.amazonaws.com/241nm/uploads/67132_perchlorate_isotherm.jpg' alt='' />MTP and TF contributed equally to this work.(1) de Graaff, C.; Ruijter, E.; Orru, R. V. A. Chem. Soc. Rev. 2012 , 41, 3969.(2) Le Quement, S. T.; Flagstad, T.; Mikkelsen, R. J. T.; Hansen, M. R.; Givskov, M. C.; Nielsen, T. E. Org. Lett. 2012 , 14, 640.(3) For a recent report, see:, Denis, J. D. St.; Scully, C. C. G.; Lee, C. F.; Yudin, A. K. Org. Lett. 2014 , 16, 1338.(4) Dimitrijevic, E.; Taylor, M. S. ACS Catal. 2013 , 3, 945.

Synthesis of novel boron heterocycles via a Petasis-type 4-component reaction

248th National Meeting (2014)

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