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

Francesco Montalbano; Nuno R. Candeias; Luis F. Veiros; Vania Andre; M. Teresa Duarte; Maria R. Bronze; Rui Moreira; Pedro M. P. Gois

doi:10.1021/ol203224n

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

Francesco Montalbano
, Nuno R. Candeias
, Luis F. Veiros
, Vania Andre
, M. Teresa Duarte
, Maria R. Bronze
, Rui Moreira
, Pedro M. P. Gois^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Scientific › peer-review

28 Citations (Scopus)

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.

Original language	English
Pages (from-to)	988-991
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	4
DOIs	https://doi.org/10.1021/ol203224n
Publication status	Published - 17 Feb 2012
Publication type	A1 Journal article-refereed

Funding

Fundacao para a Ciencia e Tecnologia (PTDC/QUI-QUI/118315/2010; PTDC/QUI-QUI/099389/2008; FRH/BPD/46589/2008;/48219/2008; Pest-OE/SAU/UI4013/2011; PEst-OE/QUI/UI0100/2011) are acknowledged for financial support.

Keywords

BORON
COMPLEXES
NITROGEN

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10.1021/ol203224n

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title = "Four-Component Assembly of Chiral N-B Heterocycles with a Natural Product-Like Framework",

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.",

keywords = "BORON, COMPLEXES, NITROGEN",

author = "Francesco Montalbano and Candeias, \{Nuno R.\} and Veiros, \{Luis F.\} and Vania Andre and Duarte, \{M. Teresa\} and Bronze, \{Maria R.\} and Rui Moreira and Gois, \{Pedro M. P.\}",

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doi = "10.1021/ol203224n",

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T1 - Four-Component Assembly of Chiral N-B Heterocycles with a Natural Product-Like Framework

AU - Montalbano, Francesco

AU - Candeias, Nuno R.

AU - Veiros, Luis F.

AU - Andre, Vania

AU - Duarte, M. Teresa

AU - Bronze, Maria R.

AU - Moreira, Rui

AU - Gois, Pedro M. P.

PY - 2012/2/17

Y1 - 2012/2/17

N2 - 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.

AB - 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.

KW - BORON

KW - COMPLEXES

KW - NITROGEN

U2 - 10.1021/ol203224n

DO - 10.1021/ol203224n

M3 - Article

SN - 1523-7060

VL - 14

SP - 988

EP - 991

JO - Organic Letters

JF - Organic Letters

IS - 4

ER -

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

Abstract

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Keywords

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