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Totally Selective Reaction of CO₂ with Enantiopure Amino Epoxides under Mild Reaction Conditions. Synthesis and Synthetic Applications of Enantiopure (4R,1‘S)- or (4S,1‘S)-4-(1-Aminoalkyl)-2-oxo-1,3-dioxolanes

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José M. Concellón* and Virginia del Solar

Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, Julián Clavería, 8, 33071 Oviedo, Spain

Santiago García-Granda and M. Rosario Díaz

Departamento de Química Física y Analítica, Facultad de Química, Universidad de Oviedo, Julián Clavería, 8, 33071 Oviedo, Spain

J. Org. Chem., 2007, 72 (20), pp 7567–7573

DOI: 10.1021/jo070829x

Publication Date (Web): August 24, 2007

Abstract

The reaction of chiral (2R,1‘S)- or (2S,1‘S)-2-(1-aminoalkyl)epoxides 1 or 2 with CO₂, generated from acidic treatment of an aqueous solution of NaHCO₃ at room temperature, efficiently afforded enantiopure cyclic carbonates 3 or 4, respectively, with total selectivity. Compounds 3 and 4 were readily transformed into the corresponding diols 7 and 8 by reaction with LiAlH₄ or by basic hydrolysis. When compounds 3 or 4 were allowed to react with methyllithium at −78 °C, O¹-acetylalkane-1,2-diols 9 and 10 were obtained with total or high selectivity.

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This article has been cited by 1 ACS Journal articles (1 most recent appear below).

Efficient and Highly Selective Synthesis of Enantiopure cis- or trans-3,4-Disubstituted 1,2,3,4-Tetrahydroisoquinolines
José M. Concellón, Paula Tuya, Virginia del Solar, Santiago García-Granda and M. Rosario Díaz
Organic Letters2009 11 (16), 3750-3753
- Efficient and Highly Selective Synthesis of Enantiopure cis- or trans-3,4-Disubstituted 1,2,3,4-Tetrahydroisoquinolines
  José M. Concellón, Paula Tuya, Virginia del Solar, Santiago García-Granda and M. Rosario Díaz
  Organic Letters2009 11 (16), 3750-3753
  An efficient synthesis of enantiopure 3,4-disubstituted 1,2,3,4-tetrahydroisoquinolines, by treatment of readily available (2R,1′S)- or (2S,1′S)-2-(1-aminoalkyl)epoxides with H3PO4·BF3 complex, under mild reaction conditions, is reported. Both ...
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History

Published In Issue September 28, 2007
Received May 18, 2007

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Article

Totally Selective Reaction of CO₂ with Enantiopure Amino Epoxides under Mild Reaction Conditions. Synthesis and Synthetic Applications of Enantiopure (4R,1‘S)- or (4S,1‘S)-4-(1-Aminoalkyl)-2-oxo-1,3-dioxolanes

Abstract

Citing Articles

Efficient and Highly Selective Synthesis of Enantiopure cis- or trans-3,4-Disubstituted 1,2,3,4-Tetrahydroisoquinolines