Scope and limitations of the aromatic anionic [1,3] P-O to P-C rearrangement in the synthesis of chiral o-hydroxyaryl diazaphosphonamides

Tetrahedron

Volumn 56, Issue 4, 2000, Pages 595-603

  Legrand, Olivier ^a   Brunel, Jean Michel ^a   Buono, Gérard ^a  

^a Procedes d'Ingenierie Chimiques d'A   (France)

Author keywords

Enantioselective catalysis; Non organometallic phosphorous reagents; Stereoselectivity

Indexed keywords

AMIDE; AROMATIC COMPOUND; CARBON; OXYGEN; PHOSPHORUS;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034695582     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00966-7     Document Type: Article

References (24)

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7. On the other hand, treatment of such precursors prepared from (S)-2-anilinomethyl pyrrolidine with an excess of LDA led to the formation of products resulting from an original ring-expansion reaction of the diazaphospholidine ring via a totally stereospecific P-N to P-C migration rearrangement. Legrand, O.; Brunel, J. M.; Buono, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1479.
8. The notations of the syn and anti diastereomers are according to the methylene substituent of the pyrrolidine ring with respect to the extracyclic aryl group. If they are at the same side of the five membered phosphorus-containing ring, we call it a syn diastereomer; otherwise, it is an anti diastereomer. (a) Cros, P.; Buono, G.; Peiffer, G.; Denis, D.; Mortreux, A.; Petit, F. New J. Chem. 1987, 11, 573.
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12. -3. The space group was determined to be C2/c from the systemic absences. A total of 3098 reflections were collected at T=298 K. The standards were measured after every 120 reflections. Among the first 200 pairs of reflections, the signs of the corresponding calculated differences, establishing that the molecule is described with the correct absolute configuration S. CCDC 132971.
13. - according to Mikolajczyk et al.: (a) Mikolajczyk, M.; Omelanzuk, J.; Paru, M. Tetrahedron 1972, 28, 3855 and references cited therein.
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