M. A. Jalil, E. B. Hui / Tetrahedron Letters 47 (2006) 1473–1475
1475
Li
O
PPh2Li
THF
O
O
O
O
S
S
Ph2P
O
S
S
S
THF
OLi
O
6 (72%)
1
Scheme 4. Synthesis of ligand 6 containing a S-heterocycle.
Chem. Rev. 2000, 100, 1169; (d) Mecking, S. Coord. Chem.
Rev. 2000, 203, 325; (e) Braunstein, P.; Fryzuk, M. D.;
Dall, M. L.; Naud, F.; Rettig, S. J.; Speiser, F. Dalton
2000, 1067.
In conclusion, we have reported a simple reaction for the
preparation of a variety of P,N and P,S ligands contain-
ing various N- and S-heterocycles. The synthetic strat-
egy can be extended to other heterocyclic-phosphine
ligands. The procedure allows the steric and electronic
properties of ligands to be fine tuned by choosing differ-
ent cyclic sulfates and by changing the substituents on
the phosphorus or the heterocyclic ring.
5. For recent reviews on chiral P,N-ligands; see: (a) Chelucci,
`
G.; Orru, G.; Pinna, G. A. Tetrahedron 2003, 59, 9471;
(b) Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33,
336.
6. McManus, H. A.; Guiry, P. J. Chem. Rev. 2004, 104, 4151.
7. Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110,
7538.
8. (a) Byun, H.-S.; He, L.; Bittman, R. Tetrahedron 2000, 56,
7051; (b) Lohray, B. B. Synthesis 1992, 1035; (c) Lohray,
B. B.; Bhushan, V. Adv. Heterocycl. Chem. 1997, 68, 89.
9. (a) Lohray, B. B.; Bhushan, V. Adv. Heterocycl. Chem.
1997, 68, 89; (b) Vanhessche, K. P. M.; Sharpless, K. B.
Chem. Eur. J. 1997, 3, 517.
10. (a) Leurquin, F.; Ozturk, T.; Pilkington, M.; Wallis, J. D.
J. Chem. Soc., Perkin Trans. 1 1997, 3173; (b) Calvo-
Flores, F.; Garcia-Mendoza, P.; Hernandez-Mateo, F.;
Isac-Garcia, J.; Santoyo-Gonzalez, F. J. Org. Chem. 1997,
62, 3944; (c) Oi, R.; Sharpless, K. B. Tetrahedron Lett.
1991, 32, 999.
11. Werner’s group reported several 1,2-bis(phospha-
nyl)ethanes and 1,2-arsanyl(phosphanyl)ethanes by using
similar cyclic sulfate: (a) Fries, G.; Wolf, J.; Pfeiffer, M.;
Stalke, D.; Werner, H. Angew. Chem., Int. Ed. 2000, 39,
564; (b) Fries, G.; Wolf, J.; Ilg, K.; Walfort, B.; Stalke, D.;
Werner, H. Dalton Trans. 2004, 1873.
Acknowledgments
We gratefully thank Dr. Christina Chai of ICES for her
support. We thank the Agency for Science, Technology
and Research (A STAR) of Singapore under the project
*
code ICES 03-141005 for financial support.
Supplementary data
Supplementary data (synthetic and spectroscopic data
for the compounds 2a–b, 4, 5, and 6) associated with this
article can be found, in the online version, at doi:10.1016/
References and notes
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cam.ac.uk.
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