Ligand tuning in asymmetric catalysis: Mono- and bis-phospholanes for a prototypical Pd-catalyzed asymmetric allylation reaction

Organic Letters

Volumn 2, Issue 2, 2000, Pages 199-202

  Yan, Yuan Yong ^a   RajanBabu, T V ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000576678     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991285r     Document Type: Article

References (61)

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53. For a complete listing of the ligands used, see refs 9a-c.
54. 2c reported the synthesis of ligand 3 and application of one of its derivatives to Rh(1)-catalyzed asymmetric hydrogenation.
55. (a) DIOP (2,2-dimethyl-1,3-dioxalane-4,5-diylbismethylene)bisdiphenylphosphine): Dang, T.-P.; Kagan, H. B. J. Chem. Soc., Chem Commun. 1971, 481. See also: Kagan, H. B. Chiral Ligands for Asymmetic Catalysis. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1985; Vol. 5, pp 1-39.
56. (a) DIOP (2,2-dimethyl-1,3-dioxalane-4,5-diylbismethylene)bisdiphenylphosphine): Dang, T.-P.; Kagan, H. B. J. Chem. Soc., Chem Commun. 1971, 481. See also: Kagan, H. B. Chiral Ligands for Asymmetic Catalysis. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1985; Vol. 5, pp 1-39.
57. (b) Another analogue, 12, has already been described in the literature: Kagan, H. B.; Fiaud, J. C.; Hoornaert, C.; Meyer, D.; Poulin, J. C. Bull. Soc. Chem. Belg. 1979, 88, 923.
58. DIOP itself gave nearly racemic products in the allylation reaction, see: (c) Hayashi, T.; Yamamoto, A.; Hagihara, T.; Ito, Y. Tetrahedron Lett. 1986, 27, 191.
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60. (e) Reference 9o.
61. 2/hexane, 1/1, v/v) to afford the malonate product in nearly quantitative yield. The enantiomeric excess was determined by HPLC. For dimethyl (1,3-diphenylprop-2-en-1-yl)malonate: Chiralcel OD-H column, eluent hexane/PrOH 98/2, flow rate 0.5 mL/min. For diethyl (1,3-diphenylprop-2-en-1-yl)malonate: OJ column, eluent hexane/PrOH 95/5, flow rate 0.5 mL/min. Some variations of ee's as a function of solvent, temperature, and the nature of the nucleophile were observed. For a more complete listing of reactions examined, see Supporting Information.