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García Ruano JL, Alemán J, Soriano JF. Facile synthesis of optically pure 1,2-diaryl (and 1-Alkyl-2-aryl) ethyl and propylamines. Org Lett. 2003;5(5):677-80doi: 10.1021/ol027464h.
García Ruano, J. L., Alemán, J., & Soriano, J. F. (2003). Facile synthesis of optically pure 1,2-diaryl (and 1-Alkyl-2-aryl) ethyl and propylamines. Organic letters, 5(5), 677-80. https://doi.org/10.1021/ol027464h
García Ruano, José L, et al. "Facile synthesis of optically pure 1,2-diaryl (and 1-Alkyl-2-aryl) ethyl and propylamines." Organic letters vol. 5,5 (2003): 677-80. doi: https://doi.org/10.1021/ol027464h
García Ruano JL, Alemán J, Soriano JF. Facile synthesis of optically pure 1,2-diaryl (and 1-Alkyl-2-aryl) ethyl and propylamines. Org Lett. 2003 Mar 06;5(5):677-80. doi: 10.1021/ol027464h. PMID: 12605488.
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Org Lett. 2003 Mar 06;5(5):677-80. doi: 10.1021/ol027464h.

Facile synthesis of optically pure 1,2-diaryl (and 1-Alkyl-2-aryl) ethyl and propylamines.

Organic letters

José L García Ruano, José Alemán, José F Soriano

Affiliations

  1. Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain. [email protected]

PMID: 12605488 DOI: 10.1021/ol027464h

Abstract

A concise high-yielding route to synthetically useful 1,2-diaryl (and 1-alkyl-2-aryl) ethyl and propylamines in high enantiomeric purity is described. The key step of this route is the completely stereoselective addition of lithium (R)-ortho-(p-toluenesulfinyl)benzylic carbanions to (S)-N-p-toluenesulfinylimines, which takes place in very high or quantitative yields. N-Desulfinylation and C-desulfinylation of the resulting adducts can be achieved with no loss of optical purity employing conventional methods (TFA and Raney-Ni, respectively).

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