Synthesis and Structural Characterization of Trivalent Amino Acid Derived Chiral Phosphorus Compounds
| Autor: | Ping Xu, Brian Bickford, Mohammad Salman Hamdani, Thomas F. Wood, William H. Hersh, Cheslan K. Simpson, Arnold L. Rheingold, Jonathan E. Grob |
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| Rok vydání: | 2004 |
| Předmět: | |
| Zdroj: | The Journal of Organic Chemistry. 69:2153-2163 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo035508+ |
| Popis: | Reaction of the N-toluenesulfonyl derivatives of (S)-alanine, phenylalanine, and valine (4−6) with PhPCl2 gave in high yield the 4-methyl, benzyl, and isopropyl derivatives (7−9) of 2-phenyl-1-p-toluenesulfonyl-1,3,2-oxazaphospholidin-5-one. The ratios of the (2S,4S)/(2R,4S) diastereomers (cis/trans isomers) were 1:1, 2:1, and 10:1 for the methyl, benzyl, and isopropyl derivatives 7a,b, 8a,b, and 9a,b, respectively. For 7a,b, both isomers could be crystallized, but for the others only the major isomers were isolable. The X-ray crystal structure of 9a shows that the isopropyl and phenyl groups are mutually cis and that the tolyl moiety is oriented s-trans to both the isopropyl and phenyl groups. Reaction of 6 with Cl2PCH2CH2PCl2 (10) gave a 56:38:7 mixture of the cis/cis, cis/trans, and trans/trans diphosphorus heterocycles 11a−c. The major isomer could be crystallized and isolated free of the other diastereomers. Reaction of 6 with EtPCl2 gave a 6:1 mixture of cis/trans isomers of the ethyl-substituted he... |
| Databáze: | OpenAIRE |
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