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: |
|
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.pitt.edu/id/eprint/17530 |
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