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Synthesis of highly enantioenriched 3,4-dihydroquinolin-2-ones by 6-Exo-trig radical cyclizations of axially chiral α-halo-ortho-alkenyl anilides

Guthrie, DB and Geib, SJ and Curran, DP (2009) Synthesis of highly enantioenriched 3,4-dihydroquinolin-2-ones by 6-Exo-trig radical cyclizations of axially chiral α-halo-ortho-alkenyl anilides. Journal of the American Chemical Society, 131 (42). 15492 - 15500. ISSN 0002-7863

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Abstract

Radical cyclizations (Bu3SnH, Et3B/air, rt) of racemic R-halo-ortho-alkenyl anilides provide 3,4-dihydroquinolin-2-ones in high yield. Cyclizations of enantioenriched precursors occur in similarly high yields and with transfer of axial chirality to the new stereocenter of the products with exceptionally high fidelity (often >95%). Single and tandem cyclizations of α-halo-ortho-alkenyl anilides bearing an additional substituent on the α-carbon occur with high chirality transfer and high diastereoselectivity. Straightforward models are proposed to interpret both the chirality transfer and diastereoselectivity aspects. These first examples of an approach for axial chiral transfer from a reactive species in the amide to an acceptor suggest broad potential for extension both within and beyond radical reactions. © 2009 American Chemical Society.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Guthrie, DB
Geib, SJgeib@pitt.eduGEIB0000-0002-9160-7857
Curran, DPcurran@pitt.eduCURRAN
Date: 28 October 2009
Date Type: Publication
Journal or Publication Title: Journal of the American Chemical Society
Volume: 131
Number: 42
Page Range: 15492 - 15500
DOI or Unique Handle: 10.1021/ja9066282
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0002-7863
MeSH Headings: Alkenes--chemistry; Anilides--chemistry; Crystallography, X-Ray; Cyclization; Free Radicals--chemistry; Models, Molecular; Molecular Structure; Quinolones--chemical synthesis; Stereoisomerism
Other ID: NLM NIHMS150630, NLM PMC2784126
PubMed Central ID: PMC2784126
PubMed ID: 19799432
Date Deposited: 18 Feb 2013 15:34
Last Modified: 02 Feb 2019 15:59
URI: http://d-scholarship.pitt.edu/id/eprint/17331

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