Improved catalytic asymmetric carbon-carbon bond formation using combinations of chiral and achiral monodentate ligands

Tetrahedron Asymmetry

Volumn 16, Issue 11, 2005, Pages 1901-1904

  Duursma, Ate ^a   Peña, Diego ^a   Minnaard, Adriaan J ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; LIGAND; PHOSPHORAMIDOUS ACID DERIVATIVE; RHODIUM;

ADDITION REACTION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CHEMICAL BOND; CHIRALITY; ENANTIOSELECTIVITY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL;

EID: 20444391382     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.05.006     Document Type: Article

References (24)

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4. M.T. Reetz Chimia Oggi 21 2003 5 8
5. For an early example using mixtures of bidentate ligands see: B. Kaptein, H. Elsenberg, A.J. Minnaard, Q.B. Broxterman, L.A. Hulshof, J. Koek, and T.R. Vries Tetrahedron: Asymmetry 10 1999 1413 1418
6. Ref. 1
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10. For an extension of this concept using a dynamic library, see: C. Monti, C. Gennari, and U. Piarulli Tetrahedron Lett. 45 2004 6859 6862
11. A. Duursma, R. Hoen, J. Schuppan, R. Hulst, A.J. Minnaard, and B.L. Feringa Org. Lett. 5 2003 3111 3113
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13. Ref. 2b
14. 2P 209.060. Found 209.060. Phosphoramidite ligands L4 and L5 have been reported before, see: L.A. Arnold, R. Imbos, A. Mandoli, A.H.M. De Vries, R. Naasz, and B.L. Feringa Tetrahedron 56 2000 2865 2878
15. and were prepared according to a recently reported procedure: J.G. Boiteau, A.J. Minnaard, and B.L. Feringa J. Org. Chem. 68 2003 9481 9484
16. Ligand L6 has been reported before, see: A. Alexakis, S. Rosset, J. Allamand, S. March, F. Guillen, and C. Benhaim Synlett 2001 1375 1378
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22. J.G. Boiteau, A.J. Minnaard, and B.L. Feringa J. Org. Chem. 68 2003 9481 9484
23. 4, and subjected to GC and HPLC analysis. For 3: enantiomer separation by HPLC on a Chiralpak OD column, heptanes-isopropanol 99/1, 210 nm, 12.7/14.3 min. For 5: Enantiomer separation by GC on a Chiraldex A-TA column, 30 m × 0.25 mm × 0.12 μm, 120°C isothermic, 58.0/60.1 min. For spectroscopic data of 3 and 5 see Ref. 7a.
24. Imbalance in homo-complex ratios is due to errors in weighing