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American Chemical Society, Organic Letters, 4(14), p. 988-991, 2012

DOI: 10.1021/ol203224n

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Four-Component Assembly of Chiral N-B Heterocycles with a Natural Product-Like Framework

Journal article published in 2012 by Francesco Montalbano, Nuno R. Candeias ORCID, Luís F. Veiros ORCID, Vânia André ORCID, M. Teresa Duarte ORCID, M. Teresa Duarte, Maria R. Bronze, Rui Moreira ORCID, Pedro M. P. Gois ORCID
This paper is available in a repository.
This paper is available in a repository.

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Abstract

The dative N-B bond was used to simply assemble heterocycles with a skeleton akin to the 5-oxofuro[2,3-b]furan motif. Twenty-five new N-B heterocycles were prepared via a highly efficient one-pot four-component reaction in yields and diastereoselectivities up to 95% and >97%, respectively. Several reaction intermediates were discovered using electrospray ionization mass spectroscopy which set the basis for the mechanism elucidation using DFT calculations.