Cross-metathesis, a versatile synthetic methodology for the construction of alkenyl phosphine oxides and bis-phosphine oxides

Tetrahedron Letters

Volumn 44, Issue 38, 2003, Pages 7133-7135

  Bisaro, F ^a   Gouverneur, V ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKENYL GROUP; OXIDE; PHOSPHINE DERIVATIVE;

ARTICLE; RING CLOSING METATHESIS; STEREOCHEMISTRY; SYNTHESIS; TECHNIQUE;

EID: 0041508521     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01842-2     Document Type: Article

References (19)

1. For various applications, see for example: (a) Brunner, H.; Limmer, S. J. Organomet. Chem. 1991, 417, 173-180; (b) Brunner, H.; Limmer, S. J. Organomet. Chem. 1991, 413, 55-63; (c) Nicolaou, K. C.; Maligres, P.; Shin, J.; de Leon, E.; Rideout, D. J. Am. Chem. Soc. 1990, 112, 7825-7826; (d) Haynes, R. K.; Loughlin, W. A.; Hambley, T. W. J. Org. Chem. 1991, 56, 5785-5790.
2. For various applications, see for example: (a) Brunner, H.; Limmer, S. J. Organomet. Chem. 1991, 417, 173-180; (b) Brunner, H.; Limmer, S. J. Organomet. Chem. 1991, 413, 55-63; (c) Nicolaou, K. C.; Maligres, P.; Shin, J.; de Leon, E.; Rideout, D. J. Am. Chem. Soc. 1990, 112, 7825-7826; (d) Haynes, R. K.; Loughlin, W. A.; Hambley, T. W. J. Org. Chem. 1991, 56, 5785-5790.
3. For various applications, see for example: (a) Brunner, H.; Limmer, S. J. Organomet. Chem. 1991, 417, 173-180; (b) Brunner, H.; Limmer, S. J. Organomet. Chem. 1991, 413, 55-63; (c) Nicolaou, K. C.; Maligres, P.; Shin, J.; de Leon, E.; Rideout, D. J. Am. Chem. Soc. 1990, 112, 7825-7826; (d) Haynes, R. K.; Loughlin, W. A.; Hambley, T. W. J. Org. Chem. 1991, 56, 5785-5790.
4. For various applications, see for example: (a) Brunner, H.; Limmer, S. J. Organomet. Chem. 1991, 417, 173-180; (b) Brunner, H.; Limmer, S. J. Organomet. Chem. 1991, 413, 55-63; (c) Nicolaou, K. C.; Maligres, P.; Shin, J.; de Leon, E.; Rideout, D. J. Am. Chem. Soc. 1990, 112, 7825-7826; (d) Haynes, R. K.; Loughlin, W. A.; Hambley, T. W. J. Org. Chem. 1991, 56, 5785-5790.
5. (a) Zhao C.-Q., Han L.-B., Goto M., Tanaka M. Angew. Chem., Int. Ed. 40:2001;1929-1932.
6. (b) Han L.-B., Zhao C.-Q., Tanaka M. J. Org. Chem. 66:2001;5929-5932. and references cited therein.
7. (a) Connon S.J., Blechert S. Angew. Chem., Int. Ed. 42:2003;1900-1923.
8. (b) Gibson S.E., Keen S.P. Top. Organomet. Chem. 1:1998;155-181.
9. (c) Mori M. Top. Organomet. Chem. 1:1998;133-154.
10. (d) Blackwell H.E., O'Leary D.J., Chatterjee A.K., Washenfelder R.A., Bussmann D.A., Grubbs R.H. J. Am. Chem. Soc. 122:2000;58-71.
11. Chatterjee A.K., Choi T.-L., Grubbs R.H. Synlett. 2001;1034-1037.
12. Lera M., Hayes C.J. Org. Lett. 3:2001;2765-2768.
13. Dean Toste F., Chatterjee A.K., Grubbs R.H. Pure Appl. Chem. 74:2002;7-10.
14. (a) Trevitt M., Gouverneur V. Tetrahedron Lett. 40:1999;7333-7336.
15. (b) Schuman M., Trevitt M., Redd A., Gouverneur V. Angew. Chem., Int. Ed. 39:2000;2491-2493.
16. Scholl M., Ding S., Woo Lee C., Grubbs R.H. Org. Lett. 1:1999;953-956.
17. For similar observations with α,β-unsaturated carbonyl compounds, see: Choi T.-L., Chatterjee A.K., Grubbs R.H. Angew. Chem., Int. Ed. 40:2001;1277-1279. and references therein.
18. P,H=20 Hz for E isomers, see: Williams D.H., Fleming I. Spectroscopic Methods in Organic Chemistry. 5th Ed. 1995;168 McGraw-Hill, London.
19. For these reactions (entries 5 and 6, Table 2), one of the olefins is used in excess (3 equiv.).