Investigation into an asymmetric hydrogenation promoted by rhodium-phosphetane complexes

Tetrahedron Letters

Volumn 40, Issue 48, 1999, Pages 8365-8368

  Marinetti, Angela ^a   Jus, Sébastien ^a   Genêt, Jean Pierre ^a  

^a PSL RESEARCH UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; HYDROGEN; PHOSPHINE DERIVATIVE; RHODIUM COMPLEX;

ARTICLE; CATALYSIS; CHIRALITY; ENANTIOMER; HYDROGENATION; PRESSURE;

EID: 0033607585     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01767-0     Document Type: Article

References (18)

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4. D +16 (c 2, MeOH)] and HPLC retention times, by comparison with known compounds.
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6. 2). Compound (S,S)-2 has been prepared from 1,2-bis(phosphino)ethane and the cyclic sulfate of (R,R)-1,3-dicyclohexylpropanediol. The detailed procedure will be reported later.
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13. For instance, the equatorial phenyl groups of (R)-Binap in the λ conformation induce sterical hindrance in the upper-left and bottom-right space quadrants (P-chirality). (formula presented) In the rhodium catalysed hydrogenations, (R)-Binap affords (S)-N-acetylphenylalanine derivatives. Noyori, R. Chem. Soc. Rev. 1989, 18, 187. See, also: Sakuraba, S.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1991, 2, 597.
14. For instance, the equatorial phenyl groups of (R)-Binap in the λ conformation induce sterical hindrance in the upper-left and bottom-right space quadrants (P-chirality). (formula presented) In the rhodium catalysed hydrogenations, (R)-Binap affords (S)-N-acetylphenylalanine derivatives. Noyori, R. Chem. Soc. Rev. 1989, 18, 187. See, also: Sakuraba, S.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1991, 2, 597.
15. Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125. It must be noticed, however, that previous mechanistic work suggests that DuPHOS-based catalysts follow the usual hydrogenation pathway, where the minor substrate-rhodium complex affords the predominant final product: Armstrong, S. K.; Brown, J. M.; Burk, M. J.Tetrahedron Lett. 1993, 34, 879.
16. Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125. It must be noticed, however, that previous mechanistic work suggests that DuPHOS-based catalysts follow the usual hydrogenation pathway, where the minor substrate-rhodium complex affords the predominant final product: Armstrong, S. K.; Brown, J. M.; Burk, M. J. Tetrahedron Lett. 1993, 34, 879.
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18. 3) was obtained at high pressure. The absolute stereochemistry of the major isomer is assumed to be (2R,3S) by analogy to the stereochemical issue of the reported DuPHOS catalysed hydrogenation of the N-acetyl derivative: Burk, M. J.; Gross, M. F.; Martinez, J. P. J. Am. Chem. Soc. 1995, 117, 9375.