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Volumn 38, Issue 10, 1999, Pages 1479-1483

Stereospecific migration of P from N to Csp2: Ring-expansion reaction of chiral diazaphospholidine oxides

Author keywords

Asymmetric synthesis; Intermediates; Phosphorus; Rearrangements; Ring expansions

Indexed keywords

DIAZAPHOSPHOLIDINE OXIDE; OXIDE; UNCLASSIFIED DRUG;

EID: 0033577817     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19990517)38:10<1479::aid-anie1479>3.0.co;2-g     Document Type: Article
Times cited : (17)

References (73)
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    • b) D. Hellwinkel, G. Hofmann, F. Lammerzahl, Tetrahedron Lett. 1977, 37, 3241. In these cases, the migrations occur at the phenol N-methylaniline ring upon use of a large excess of LDA. It clearly appears that the N→C migrations occur only after the O→C migrations have been completed.
    • (1977) Tetrahedron Lett. , vol.37 , pp. 3241
    • Hellwinkel, D.1    Hofmann, G.2    Lammerzahl, F.3
  • 42
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    • The notations of the syn and anti diastereomers are according to the methylene substituent of the pyrrolidine ring with respect to the exocyclic 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) P. Cros, G. Buono, G. Peiffer, D. Denis, A. Mortreux, F. Petit, New. J. Chem. 1987, 11, 573;
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    • Cros, P.1    Buono, G.2    Peiffer, G.3    Denis, D.4    Mortreux, A.5    Petit, F.6
  • 45
    • 33745153400 scopus 로고    scopus 로고
    • note
    • -3. A total of 2155 reflections were collected at T = 298 K. The standards were measured after every 655 reflections. Among the first 20 pairs of reflections, the signs of the corresponding calculated differences established that the molecule is described with the correct absolute configuration. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-112627. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam. ac.uk).
  • 51
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    • Mechanism and Catalysis of Nucleophilic Substitution in Phosphate Esters
    • (Ed.: D. Betheil), Academic Press, New York
    • Owing to the stability of some pentacoordinate square-pyramidal (SP) phosphorus species, it is also possible to consider mechanistic pathways proceeding via SP intermediates with the four-membered oxaphosphetane ring and the five-membered diazaphospholane ring in basal positions and the oxygen anion group in an axial position. The stereochemistry of the migration derives from a cis basal interaction of the entering/leaving group; see also G. R. J. Thatcher, R. Kluger, Mechanism and Catalysis of Nucleophilic Substitution in Phosphate Esters in Advances in Physical Organic Chemistry, Vol. 25 (Ed.: D. Betheil), Academic Press, New York, 1989, pp. 99-265.
    • (1989) Advances in Physical Organic Chemistry , vol.25 , pp. 99-265
    • Thatcher, G.R.J.1    Kluger, R.2
  • 53
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    • Such phosphetane intermediates have played an important role in the elucidation of factors that influence the stereochemistry of the Wittig reaction: a) B. E. Maryanoff, A. B. Reitz, Chem. Rev. 1989, 89, 863;
    • (1989) Chem. Rev. , vol.89 , pp. 863
    • Maryanoff, B.E.1    Reitz, A.B.2
  • 58
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    • Isolable 1,2-oxaphosphetanes were synthesized, and X-ray crystrallographic analysis was performed to determinate the structure of such compounds. a) T. Kawashima, K. Kato, R. Okazaki, Angew. Chem. 1993, 105, 941;
    • (1993) Angew. Chem. , vol.105 , pp. 941
    • Kawashima, T.1    Kato, K.2    Okazaki, R.3
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    • ACS Monograph 176, American Chemical Society, Washington, DC
    • R. R. Holmes, Pentacoordinated Phosphorus, Vol. 2, ACS Monograph 176, American Chemical Society, Washington, DC, 1980.
    • (1980) Pentacoordinated Phosphorus , vol.2
    • Holmes, R.R.1
  • 70
    • 33745124680 scopus 로고    scopus 로고
    • note
    • AM1 calculations (AMPAC version 2.20) also clearly indicate the favored formation of intermediate TS2 (heat of formation 18.46 kcal) over TS1 (heat of formation 140.22 kcal).
  • 71
    • 0042990375 scopus 로고
    • Previous investigations have been carried out on the sterochemical behavior of the four-membered oxyphosphoranes (1,2-oxaphosphetanes) having three P-C bonds: a) F. Ramirez, J. F. Pilot, O. P. Madan, C. P. Smith, J. Am. Chem. Soc. 1968, 90, 1275;
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 1275
    • Ramirez, F.1    Pilot, J.F.2    Madan, O.P.3    Smith, C.P.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.