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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Abstract

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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Details

Item Type:	Article
Status:	Published
Creators/Authors:	Creators Email Pitt Username ORCID Guthrie, DB Curran, DP curran@pitt.edu CURRAN
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
URI:	http://d-scholarship-dev.library.pitt.edu/id/eprint/17530

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