Regio- and enantioselective molybdenum-catalyzed alkylations of polyenyl esters [1]

Journal of the American Chemical Society

Volumn 121, Issue 44, 1999, Pages 10416-10417

  Trost, Barry M ^a   Hildbrand, Stefan ^a   Dogra, Kalindi ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER; MOLYBDENUM;

ALKYLATION; LETTER; STEREOCHEMISTRY;

EID: 0033544297     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992602s     Document Type: Letter

References (22)

1. (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1998, 120, 70.
2. (b) Nilsson, Y. I. M.; Andersson, P. G.; Backvall, J.-E. J. Am. Chem. Soc. 1993, 115, 6609.
3. (c) Andersson, P. G.; Backvall, J.-E. J. Org. Chem. 1991, 56, 5349.
4. (d) Trost, B. M.; Lautens, M.; Hung, M.-H.; Carmichael, C. S. J. Am. Chem. Soc. 1984, 106, 7641.
5. (e) Trost, B. M.; Urch, C. J.; Hung, M.-H. Tetrahedron Lett. 1986, 27, 4949.
6. Trost, B. M.; Hung, M.-H. J. Am. Chem. Soc. 1984, 106, 6837.
7. For reviews, see: Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395; Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; pp 325-365.
8. For reviews, see: Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395; Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; pp 325-365.
9. Trost, B. M.; Merlic, C. A. J. Am. Chem. Soc. 1990, 112, 9590; Trost, B. M.; Lautens, M. Tetrahedron 1987, 43, 4817; Trost, B. M.; Lautens, M. J. Am. Chem. Soc. 1987, 109, 1469; 1982, 104, 5543. Also see: Faller, J. W.; Lambert, C.; Mazzieri, M. R. J. Organomet. Chem. 1990, 383, 161; Faller, J. W.; Linebarrier, D. Organometallics 1988, 7, 1670.
10. Trost, B. M.; Merlic, C. A. J. Am. Chem. Soc. 1990, 112, 9590; Trost, B. M.; Lautens, M. Tetrahedron 1987, 43, 4817; Trost, B. M.; Lautens, M. J. Am. Chem. Soc. 1987, 109, 1469; 1982, 104, 5543. Also see: Faller, J. W.; Lambert, C.; Mazzieri, M. R. J. Organomet. Chem. 1990, 383, 161; Faller, J. W.; Linebarrier, D. Organometallics 1988, 7, 1670.
11. Trost, B. M.; Merlic, C. A. J. Am. Chem. Soc. 1990, 112, 9590; Trost, B. M.; Lautens, M. Tetrahedron 1987, 43, 4817; Trost, B. M.; Lautens, M. J. Am. Chem. Soc. 1987, 109, 1469; 1982, 104, 5543. Also see: Faller, J. W.; Lambert, C.; Mazzieri, M. R. J. Organomet. Chem. 1990, 383, 161; Faller, J. W.; Linebarrier, D. Organometallics 1988, 7, 1670.
12. Trost, B. M.; Merlic, C. A. J. Am. Chem. Soc. 1990, 112, 9590; Trost, B. M.; Lautens, M. Tetrahedron 1987, 43, 4817; Trost, B. M.; Lautens, M. J. Am. Chem. Soc. 1987, 109, 1469; 1982, 104, 5543. Also see: Faller, J. W.; Lambert, C.; Mazzieri, M. R. J. Organomet. Chem. 1990, 383, 161; Faller, J. W.; Linebarrier, D. Organometallics 1988, 7, 1670.
13. Trost, B. M.; Merlic, C. A. J. Am. Chem. Soc. 1990, 112, 9590; Trost, B. M.; Lautens, M. Tetrahedron 1987, 43, 4817; Trost, B. M.; Lautens, M. J. Am. Chem. Soc. 1987, 109, 1469; 1982, 104, 5543. Also see: Faller, J. W.; Lambert, C.; Mazzieri, M. R. J. Organomet. Chem. 1990, 383, 161; Faller, J. W.; Linebarrier, D. Organometallics 1988, 7, 1670.
14. Trost, B. M.; Merlic, C. A. J. Am. Chem. Soc. 1990, 112, 9590; Trost, B. M.; Lautens, M. Tetrahedron 1987, 43, 4817; Trost, B. M.; Lautens, M. J. Am. Chem. Soc. 1987, 109, 1469; 1982, 104, 5543. Also see: Faller, J. W.; Lambert, C.; Mazzieri, M. R. J. Organomet. Chem. 1990, 383, 161; Faller, J. W.; Linebarrier, D. Organometallics 1988, 7, 1670.
15. For work on stoichiometric π-allylmolybdenum alkylations, see: Adams, R. D.; Chodosh, D. F.; Faller, J. W.; Rosan, A. M. J. Am. Chem. Soc. 1979, 101, 2570; McCleverty, J. A.; Murray, A. J. J. Organomet. Chem. 1978, 149, C29; Rubio, A.; Liebeskind, L. S. J. Am. Chem. Soc. 1993, 115, 891.
16. For work on stoichiometric π-allylmolybdenum alkylations, see: Adams, R. D.; Chodosh, D. F.; Faller, J. W.; Rosan, A. M. J. Am. Chem. Soc. 1979, 101, 2570; McCleverty, J. A.; Murray, A. J. J. Organomet. Chem. 1978, 149, C29; Rubio, A.; Liebeskind, L. S. J. Am. Chem. Soc. 1993, 115, 891.
17. For work on stoichiometric π-allylmolybdenum alkylations, see: Adams, R. D.; Chodosh, D. F.; Faller, J. W.; Rosan, A. M. J. Am. Chem. Soc. 1979, 101, 2570; McCleverty, J. A.; Murray, A. J. J. Organomet. Chem. 1978, 149, C29; Rubio, A.; Liebeskind, L. S. J. Am. Chem. Soc. 1993, 115, 891.
18. Trost, B. M.; Hachiya, I. J. Am. Chem. Soc. 1998, 120, 1104. Also see: Glorius, F.; Pfaltz, A. Org. Lett. 1999, 1, 141.
19. Trost, B. M.; Hachiya, I. J. Am. Chem. Soc. 1998, 120, 1104. Also see: Glorius, F.; Pfaltz, A. Org. Lett. 1999, 1, 141.
20. brsm = based upon reacted starting material.
21. All new compounds have been characterized spectroscopically and elemental compositions established by combustion analysis or high-resolution mass spectrometry.
22. Prepared in standard fashion from the diamine and 4-pyrimidinecarboxylic acid [Gabriel, S.; Colman, J. Chem. Ber. 1899, 32, 1525].