Asymmetric dihydroxylation of alkenes with osmium tetroxide: Chiral N,N′-dialkyl-2,2′-bipyrrolidine complex

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 10, 1989, Pages 665-666

  Hirama, Masahiro ^a   Oishi, Tohru ^a   Itô, Shô ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049067929     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39890000665     Document Type: Article

References (10)

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4. M. Tokles and J. K. Snyder, Tetrahedron Lett., 1986, 27, 3951.
5. R. Annunziata, M. Cinquini, F. Cozzi, L. Raimondi, and S. Stefanelli, Tetrahedron Lett., 1987, 28, 3139.
6. K. Tomioka, M. Nakajima, and K. Koga, J. Am. Chem. Soc., 1987, 109, 6213.
7. E. N. Jacobsen, I. Marko, W. S. Mungali, G. Schroder, and K. B. Sharpless, J. Am. Chem. Soc., 1988, 110, 1968.
8. The optically pure (S,S)-(+)-(2) was synthesized from the readily available 2,2′-(1′-pyrrolinyl)pyrrole (H. Rapoport and N. Castagnoli, Jr., J. Am. Chem. Soc., 1962, 84, 2178) in four steps.
9. H2 (4 atom), 5% Rh/Al2O3, MeOH-AcOH (1:1).
10. PhCOCl, NEt3, CH2Cl2; chromatographic separation (SiO2) of (±)-isomer from meso-isomer (1.2:1) conc. HCl, reflux optical resolution with d-(−)-tartaric acid in MeOH-H2O (3:1).