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Asymmetric radical and anionic cyclizations of axially chiral carbamates

Guthrie, DB and Curran, DP (2009) Asymmetric radical and anionic cyclizations of axially chiral carbamates. Organic Letters, 11 (1). 249 - 251. ISSN 1523-7060

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Standard Boc, Alloc, and Cbz derivatives of N-2,4-dimethyl-6-iodophenyl-N- allyl anilines are axially chiral and can be readily resolved into atropisomers whose racemization barriers exceed 30 kcal/mol. The resolved axially chiral carbamates undergo radical and anionic cyclizations with high levels of chirality transfer from the N-Ar axis to the new stereocenter in the substituted dihydroindole products. The carbamate groups of the products are readily removed. © 2009 American Chemical Society.


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Item Type: Article
Status: Published
CreatorsEmailPitt UsernameORCID
Guthrie, DB
Curran, DPcurran@pitt.eduCURRAN
Date: 1 January 2009
Date Type: Publication
Journal or Publication Title: Organic Letters
Volume: 11
Number: 1
Page Range: 249 - 251
DOI or Unique Handle: 10.1021/ol802616u
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
MeSH Headings: Anions--chemistry; Carbamates--chemical synthesis; Carbamates--chemistry; Cyclization; Free Radicals--chemistry; Molecular Conformation; Stereoisomerism
PubMed ID: 19055374
Date Deposited: 27 Feb 2013 15:39
Last Modified: 02 Feb 2019 15:58


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