Regioselective ring opening of amino epoxides with nitriles: an easy synthesis of (2R,3S)- and (2S,3S)-1,3-diaminoalkan-2-ols with differently protected amine functions.
J Org Chem
; 70(18): 7447-50, 2005 Sep 02.
Article
em En
| MEDLINE
| ID: mdl-16122275
ABSTRACT
[reaction see text] Transformation of enantiopure (2R,1'S)- or (2S,1'S)-2-(1-aminoalkyl)epoxides 1 or 2 into the corresponding (2R,3S)- and (2S,3S)-1,3-diaminoalkan-2-ols 3 or 4 is described. The opening of the epoxide ring with different nitriles (Ritter reaction) takes place with total selectivity and in high yields in the presence of BF3.Et2O. Interestingly, the two amine groups are differently protected. A mechanism to explain this transformation is proposed.
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01-internacional
Base de dados:
MEDLINE
Assunto principal:
Inibidores da Protease de HIV
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2005
Tipo de documento:
Article
País de afiliação:
Espanha
País de publicação:
EEUU
/
ESTADOS UNIDOS
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ESTADOS UNIDOS DA AMERICA
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EUA
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UNITED STATES
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UNITED STATES OF AMERICA
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US
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USA