Enantioselective annulations for dihydroquinolones by in situ generation of azolium enolates

Anna Lee; Ashkaan Younai; Christopher K. Price; Javier Izquierdo; Rama K. Mishra; Karl A. Scheidt

doi:10.1021/ja505880r

Enantioselective annulations for dihydroquinolones by in situ generation of azolium enolates

Anna Lee, Ashkaan Younai, Christopher K. Price, Javier Izquierdo, Rama K. Mishra, Karl A. Scheidt^*

^*Corresponding author for this work

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

202 Scopus citations

Abstract

A convergent, catalytic asymmetric formal [4 + 2] annulation for the synthesis of dihydroquinolones has been developed. Carboxylic acids can be employed as precursors to NHC enolates through an in situ activation strategy. Simultaneous generation of a reactive aza-o-quinone methide under the basic conditions employed for NHC generation leads to a dual activation approach.

Original language	English (US)
Pages (from-to)	10589-10592
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	136
Issue number	30
DOIs	https://doi.org/10.1021/ja505880r
State	Published - Jul 30 2014

Funding

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja505880r

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title = "Enantioselective annulations for dihydroquinolones by in situ generation of azolium enolates",

abstract = "A convergent, catalytic asymmetric formal [4 + 2] annulation for the synthesis of dihydroquinolones has been developed. Carboxylic acids can be employed as precursors to NHC enolates through an in situ activation strategy. Simultaneous generation of a reactive aza-o-quinone methide under the basic conditions employed for NHC generation leads to a dual activation approach.",

author = "Anna Lee and Ashkaan Younai and Price, {Christopher K.} and Javier Izquierdo and Mishra, {Rama K.} and Scheidt, {Karl A.}",

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AU - Lee, Anna

AU - Younai, Ashkaan

AU - Price, Christopher K.

AU - Izquierdo, Javier

AU - Mishra, Rama K.

AU - Scheidt, Karl A.

PY - 2014/7/30

Y1 - 2014/7/30

N2 - A convergent, catalytic asymmetric formal [4 + 2] annulation for the synthesis of dihydroquinolones has been developed. Carboxylic acids can be employed as precursors to NHC enolates through an in situ activation strategy. Simultaneous generation of a reactive aza-o-quinone methide under the basic conditions employed for NHC generation leads to a dual activation approach.

AB - A convergent, catalytic asymmetric formal [4 + 2] annulation for the synthesis of dihydroquinolones has been developed. Carboxylic acids can be employed as precursors to NHC enolates through an in situ activation strategy. Simultaneous generation of a reactive aza-o-quinone methide under the basic conditions employed for NHC generation leads to a dual activation approach.

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Enantioselective annulations for dihydroquinolones by in situ generation of azolium enolates

Abstract

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CCDC 998381: Experimental Crystal Structure Determination

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Enantioselective annulations for dihydroquinolones by in situ generation of azolium enolates

Abstract

Funding

ASJC Scopus subject areas

Access to Document

Other files and links

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Datasets

CCDC 998381: Experimental Crystal Structure Determination

Cite this