STEREOCHEMISTRY AND STRUCTURE OF PHELLANPHOS AND NOPAPHOS, TWO CHIRAL DIPHOSPHINES FOR ASYMMETRIC HYDROGENATION

References

• Kagan , H. B. and Fiaud , J. C. 1978 . Topics in Stereochemistry , 10 : 175
   Google Scholar
• Horner , L. 1980 . Pure and Appl. Chem. , 52 : 843
   Web of Science ®Google Scholar
• Bosnich , B. and Fryzuk , M. D. 1981 . Topics in Stereochemistry , 12 : 119
   Google Scholar
• Caplar , V. , Comisso , G. and Sunjic , V. 1981 . Synthesis , 85
   Google Scholar
• Marko , L. and Bakos , J. 1981 . Aspects of Homogeneous Catalysis Edited by: Ugo , R. and Reidel , R. Vol. 4 , 145 Dordrecht
   Google Scholar
• Kagan , H. B. 1982 . Comprehensive Organometallic Chemistry , Edited by: Wilkinson , G. Vol. 8 , 463 Pergamon Press .
   Google Scholar
• Fryzuk , M. D. and Bosnich , B. 1977 . J. Am. Chem. Soc. , 99 : 6262
   PubMed Web of Science ®Google Scholar
• Fryzuk , M. D. and Bosnich , B. 1978 . J. Am. Chem. Soc. , 100 : 5491
   Web of Science ®Google Scholar
• Brunner , H. and Pieronczyk , W. 1979 . Angew. Chem. Int. Ed. Engl. , 18 : 620
   Web of Science ®Google Scholar
• Brunner , H. , Pieronczyk , W. , Schonhammer , B. , Streng , K. , Bernal , I. and Korp , J. 1981 . Chem. Ber. , 114 : 1137
   Google Scholar
• Nesterova , N. P. , Medved , T. T. A. , Polikerpov , Y. U. M. and Kabachnik , M. I. 1974 . Izv. Akad. Nauk. S. S. R. Khim. , 23 : 2295
   Google Scholar
• Lauer , M. , Samuel , O. and Kagan , H. B. 1979 . J. Organometal. Chem. , 177 : 309 corrigendum in J. Organomet. Chem., 185, C16 (1980)
   Web of Science ®Google Scholar
• Samuel , O. , Couffignal , R. , Lauer , M. , Zhang , S. Y. and Kagan , H. B. 1981 . Nouv. J. Chim. , 5 : 15
   Google Scholar
• Ball , R. G. and Payne , N. C. 1977 . Inorg. Chem. , 16 : 1187
   Web of Science ®Google Scholar
• Chan , A. S. C. , Pluth , J. J. and Halpern , J. 1979 . Inorg. Chimica Acta , 37 : LA 77
   Web of Science ®Google Scholar
• Halpern , J. personal communication
   Google Scholar
• Kyba , E. P. , Davis , R. E. , Juri , P. N. and Shirley , K. R. 1981 . Inorg. Chem. , 20 : 3616
   Web of Science ®Google Scholar
• Such large values are unusual for chelating 1.2-diphosphines but are common for chelating 1,4-diphosphines. For example 98° in [Rh(NBD)diop]+15, 102° and 104° in HRh(diop)2.16.
   Google Scholar
• Knowles , W. S. , Vineyard , B. D. , Sabacky , M. J. and Stults , B. R. 1980 . Fundamental Research in Homogeneous Catalysis , Edited by: Tsutsui , M. Vol. III , 537 New York : Plenum .
   Google Scholar
• Ball , R. G. , James , B. R. , Mahajan , D. and Trotter , J. 1981 . Inorg. Chem. , 20 : 254
   Web of Science ®Google Scholar
• Karplus , M. 1963 . J. Am. Chem. Soc. , 85 : 2870
   Web of Science ®Google Scholar
• Silverstein , R. M. , Bassler , G. C. and Morill , T. C. Spectrometric Identification of Organic Compounds, , fourth edition , 209 – 210 . John Wiley and Sons. .
   Google Scholar
• Bother-By , A. A. and Cox , R. H. 1969 . J. Phys. Chim. , 73 : 1830
   Web of Science ®Google Scholar
• Bucourt , R. 1974 . Topics in Stereochem. , 8 : 159
   Google Scholar
• Recently trans-1,2-bis(diphenylphosphinocyclopentane) (dpcp) and complex Ni(dpcp)Br2 were synthesized and crystal structures obtained.21 dpcp is a ligand giving a rhodium catalyst as stereoselective than the rhodium/chiraphos sytem. The dihedral angle P—C—C—P in dpcp is 161.8° (with a P—P distance of 4.450 A), in the nickel complex it has closed dramatically to 53.7° (P—P = 3.021 Å). This is additional example of a major conformational change for a flexible 1,2-diphosphine through chelation.
   Google Scholar
• Allen , D. L. , Gibson , V. C. , Green , M. L. H. , Skinner , J. F. , Bashkin , J. and Grebenik , P. D. 1983 . J. C. S. Chem. Commun. , 895
   Google Scholar
• Kessler , H. 1982 . Angew. Chem. Int. Ed. Engl. , 21 : 512 and references quoted therein
   Web of Science ®Google Scholar
• Scott , J. W. , Keith , D. D. , Nix , G. Jr. , Parrish , D. R. , Remington , S. , Roth , G. P. , Townsend , J. M. , Valentine , D. Jr. and Yang , R. 1981 . J. Org. Chem. , 46 : 5086
   Web of Science ®Google Scholar
• Couffignal , R. , Kagan , H. B. , Mathey , F. , Samuel , O. and Santini , C. 1980 . C. R. Acad. Sc. Paris , 291 : 29 Ser. C
   Google Scholar
• Santini , C. , Fisher , J. , Mathey , F. and Mitschler , A. 1980 . J. Am. Chem. Soc. , 102 : 5809
   Web of Science ®Google Scholar
• Frenz , B. A. , Schenk , M. and Olthof-Hazekamp , R. 1978 . The ENRAF-NONIUS CAD4-SDP, a real time system for concurrent X-ray data collection and crystal-structure determination . Computing in Crystallography ,
   Google Scholar