2-Aryl-4,4,8-trimethyl-2-phosphabicyclo[3.3.0]octanes: Reactive chiral phosphine catalysts for enantioselective acylation

Journal of the American Chemical Society

Volumn 121, Issue 24, 1999, Pages 5813-5814

  Vedejs, Edwin ^a   Daugulis, Olafs ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO[3.3.0]OCTANE DERIVATIVE;

ACYLATION; ALKYLATION; ARTICLE; CATALYST; CYCLIZATION; REDUCTION; STEREOCHEMISTRY;

EID: 0033597606     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990133o     Document Type: Article

References (18)

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8. For less soluble alcohols, acylations with 5b can be performed in toluene with a 2-3-fold decrease in rate and some loss in enantioselectivity, or less well in oxygenated or chlorinated solvents.
9. One possible explanation is that lower temperature increases the equilibrium concentration of 17, but other possibilities will need to be evaluated by kinetic studies.
10. 2O in toluene at -40°C.
11. Upon request from North American research groups, 15 mg samples of 14b can be provided on a limited basis to test new alcohol resolutions in exchange for data.
12. Ismagilov, R. F. J. Org. Chem. 1998, 63, 3772. The correction can become quite large if s is large because the contaminating catalyst enantiomer has high reactivity toward the (S)-alcohol, and because the (S):(R) ratio increases as conversion approaches 50%.
13. Sih, C. J.; Wu, S.-H. Top. Stereochem. 1989, 19, 63. Chen, C.-S.; Sih, C. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 695. Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114. Drueckhammer, D. G.; Hennen, W. J.; Pederson, R. L.; Barbas, C. F., III; Gautheron, C. M.; Krach, T.; Wong, C.-H. Synthesis 1991, 499. Roberts, S. M. Chimia 1993, 47, 85.
14. Sih, C. J.; Wu, S.-H. Top. Stereochem. 1989, 19, 63. Chen, C.-S.; Sih, C. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 695. Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114. Drueckhammer, D. G.; Hennen, W. J.; Pederson, R. L.; Barbas, C. F., III; Gautheron, C. M.; Krach, T.; Wong, C.-H. Synthesis 1991, 499. Roberts, S. M. Chimia 1993, 47, 85.
15. Sih, C. J.; Wu, S.-H. Top. Stereochem. 1989, 19, 63. Chen, C.-S.; Sih, C. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 695. Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114. Drueckhammer, D. G.; Hennen, W. J.; Pederson, R. L.; Barbas, C. F., III; Gautheron, C. M.; Krach, T.; Wong, C.-H. Synthesis 1991, 499. Roberts, S. M. Chimia 1993, 47, 85.
16. Sih, C. J.; Wu, S.-H. Top. Stereochem. 1989, 19, 63. Chen, C.-S.; Sih, C. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 695. Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114. Drueckhammer, D. G.; Hennen, W. J.; Pederson, R. L.; Barbas, C. F., III; Gautheron, C. M.; Krach, T.; Wong, C.-H. Synthesis 1991, 499. Roberts, S. M. Chimia 1993, 47, 85.
17. Sih, C. J.; Wu, S.-H. Top. Stereochem. 1989, 19, 63. Chen, C.-S.; Sih, C. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 695. Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114. Drueckhammer, D. G.; Hennen, W. J.; Pederson, R. L.; Barbas, C. F., III; Gautheron, C. M.; Krach, T.; Wong, C.-H. Synthesis 1991, 499. Roberts, S. M. Chimia 1993, 47, 85.
18. 2O: s < 2 for α-indanol or α-tetralol at rt.