Efficient carboazidation of alkenes using a radical desulfonylative azide transfer process.
J Am Chem Soc
; 132(49): 17511-5, 2010 Dec 15.
Article
em En
| MEDLINE
| ID: mdl-21082832
ABSTRACT
The radical-mediated carboazidation of terminal alkenes using electrophilic alkanesulfonyl azides is reported. A single reagent delivers the necessary electrophilic alkyl radical as well as the azido group, and good yields are obtained by using a moderate excess of the carboazidating reagent (1.5-2 equiv). Interestingly, in addition to the starting sulfonyl azide, this method requires only the use of a radical initiator, di-tert-butyldiazene. In terms of atom economy, this azide transfer reaction is close to ideal, as SO2 (1 equiv) is the only side product. The synthetic potential of this process has been demonstrated by a formal synthesis of the alkaloid lepadiformine C.
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1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Azidas
/
Alcaloides
/
Alcenos
Idioma:
En
Ano de publicação:
2010
Tipo de documento:
Article