First Carbamates Conversion to Amides by Simple Alkyl Group Transfer from Trialkylalanes

N-Monosubstituted carbamates are cleanly converted to amides under treatment with trialkylaluminum. This reaction involves an aluminum-assisted internal delivery of alkyl groups. It can be applied to new and mild protecting group strategies for alcohols.

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Bibliographic Details
Published inOrganic letters Vol. 6; no. 3; pp. 381 - 383
Main Authors El Kaim, Laurent, Grimaud, Laurence, Lee, Anabelle, Perroux, Yannick, Tirla, Cornelia
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.02.2004
Amer Chemical Soc
Subjects
Chemical Sciences
Chemistry
Chemistry, Organic
Organic chemistry
Physical Sciences
Science & Technology
KETONES
AGENTS
ACID
alane
amide
carbamate
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Summary:N-Monosubstituted carbamates are cleanly converted to amides under treatment with trialkylaluminum. This reaction involves an aluminum-assisted internal delivery of alkyl groups. It can be applied to new and mild protecting group strategies for alcohols.
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SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol036234f