Synthesis and Reactions of Chiral α-Lithiophosphoric Triamides

Synlett

Volumn 1997, Issue 9, 1997, Pages 1059-1060

  Müller, Jürgen F K ^a   Spingler, Bernhard ^a   Zehnder, Margareta ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0040525190     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1526     Document Type: Article

References (22)

1. For lithiation reactions of chiral benzylamine derivatives see: Zhang, P.; Gawley, R. E. Tetrahedron Lett. 1992, 33, 2945. Meyers, A. I.; Guiles, J.; Warmus, J. S.; Gonzalez, M. A. Tetrahedron Lett. 1991, 32, 5505. Huber, I. M. P.; Seebach D. Helv. Chim. Acta 1987, 67, 1944. For lithiation reactions of prochiral benzylamines in the presence of (-)-sparteine see: Park, Y. S.; Beak, P. J. Org. Chem. 1997, 62, 1574. Park, Y. S.; Boys, M. L.; Beak, P. J. Am. Chem. Soc. 1996, 118, 3757. Wu, S.; Lee, S.; Beak, P. J. Am. Chem. Soc. 1996, 118, 715. Schlosser, M.; Limat, D. J. Am. Chem. Soc. 1995, 117, 12342. Voyer, N.; Roby, J. Tetrahedron Lett. 1995, 36, 6627. Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1991, 113, 9708.
2. For lithiation reactions of chiral benzylamine derivatives see: Zhang, P.; Gawley, R. E. Tetrahedron Lett. 1992, 33, 2945. Meyers, A. I.; Guiles, J.; Warmus, J. S.; Gonzalez, M. A. Tetrahedron Lett. 1991, 32, 5505. Huber, I. M. P.; Seebach D. Helv. Chim. Acta 1987, 67, 1944. For lithiation reactions of prochiral benzylamines in the presence of (-)-sparteine see: Park, Y. S.; Beak, P. J. Org. Chem. 1997, 62, 1574. Park, Y. S.; Boys, M. L.; Beak, P. J. Am. Chem. Soc. 1996, 118, 3757. Wu, S.; Lee, S.; Beak, P. J. Am. Chem. Soc. 1996, 118, 715. Schlosser, M.; Limat, D. J. Am. Chem. Soc. 1995, 117, 12342. Voyer, N.; Roby, J. Tetrahedron Lett. 1995, 36, 6627. Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1991, 113, 9708.
3. For lithiation reactions of chiral benzylamine derivatives see: Zhang, P.; Gawley, R. E. Tetrahedron Lett. 1992, 33, 2945. Meyers, A. I.; Guiles, J.; Warmus, J. S.; Gonzalez, M. A. Tetrahedron Lett. 1991, 32, 5505. Huber, I. M. P.; Seebach D. Helv. Chim. Acta 1987, 67, 1944. For lithiation reactions of prochiral benzylamines in the presence of (-)-sparteine see: Park, Y. S.; Beak, P. J. Org. Chem. 1997, 62, 1574. Park, Y. S.; Boys, M. L.; Beak, P. J. Am. Chem. Soc. 1996, 118, 3757. Wu, S.; Lee, S.; Beak, P. J. Am. Chem. Soc. 1996, 118, 715. Schlosser, M.; Limat, D. J. Am. Chem. Soc. 1995, 117, 12342. Voyer, N.; Roby, J. Tetrahedron Lett. 1995, 36, 6627. Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1991, 113, 9708.
4. For lithiation reactions of chiral benzylamine derivatives see: Zhang, P.; Gawley, R. E. Tetrahedron Lett. 1992, 33, 2945. Meyers, A. I.; Guiles, J.; Warmus, J. S.; Gonzalez, M. A. Tetrahedron Lett. 1991, 32, 5505. Huber, I. M. P.; Seebach D. Helv. Chim. Acta 1987, 67, 1944. For lithiation reactions of prochiral benzylamines in the presence of (-)-sparteine see: Park, Y. S.; Beak, P. J. Org. Chem. 1997, 62, 1574. Park, Y. S.; Boys, M. L.; Beak, P. J. Am. Chem. Soc. 1996, 118, 3757. Wu, S.; Lee, S.; Beak, P. J. Am. Chem. Soc. 1996, 118, 715. Schlosser, M.; Limat, D. J. Am. Chem. Soc. 1995, 117, 12342. Voyer, N.; Roby, J. Tetrahedron Lett. 1995, 36, 6627. Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1991, 113, 9708.
5. For lithiation reactions of chiral benzylamine derivatives see: Zhang, P.; Gawley, R. E. Tetrahedron Lett. 1992, 33, 2945. Meyers, A. I.; Guiles, J.; Warmus, J. S.; Gonzalez, M. A. Tetrahedron Lett. 1991, 32, 5505. Huber, I. M. P.; Seebach D. Helv. Chim. Acta 1987, 67, 1944. For lithiation reactions of prochiral benzylamines in the presence of (-)-sparteine see: Park, Y. S.; Beak, P. J. Org. Chem. 1997, 62, 1574. Park, Y. S.; Boys, M. L.; Beak, P. J. Am. Chem. Soc. 1996, 118, 3757. Wu, S.; Lee, S.; Beak, P. J. Am. Chem. Soc. 1996, 118, 715. Schlosser, M.; Limat, D. J. Am. Chem. Soc. 1995, 117, 12342. Voyer, N.; Roby, J. Tetrahedron Lett. 1995, 36, 6627. Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1991, 113, 9708.
6. For lithiation reactions of chiral benzylamine derivatives see: Zhang, P.; Gawley, R. E. Tetrahedron Lett. 1992, 33, 2945. Meyers, A. I.; Guiles, J.; Warmus, J. S.; Gonzalez, M. A. Tetrahedron Lett. 1991, 32, 5505. Huber, I. M. P.; Seebach D. Helv. Chim. Acta 1987, 67, 1944. For lithiation reactions of prochiral benzylamines in the presence of (-)-sparteine see: Park, Y. S.; Beak, P. J. Org. Chem. 1997, 62, 1574. Park, Y. S.; Boys, M. L.; Beak, P. J. Am. Chem. Soc. 1996, 118, 3757. Wu, S.; Lee, S.; Beak, P. J. Am. Chem. Soc. 1996, 118, 715. Schlosser, M.; Limat, D. J. Am. Chem. Soc. 1995, 117, 12342. Voyer, N.; Roby, J. Tetrahedron Lett. 1995, 36, 6627. Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1991, 113, 9708.
7. For lithiation reactions of chiral benzylamine derivatives see: Zhang, P.; Gawley, R. E. Tetrahedron Lett. 1992, 33, 2945. Meyers, A. I.; Guiles, J.; Warmus, J. S.; Gonzalez, M. A. Tetrahedron Lett. 1991, 32, 5505. Huber, I. M. P.; Seebach D. Helv. Chim. Acta 1987, 67, 1944. For lithiation reactions of prochiral benzylamines in the presence of (-)-sparteine see: Park, Y. S.; Beak, P. J. Org. Chem. 1997, 62, 1574. Park, Y. S.; Boys, M. L.; Beak, P. J. Am. Chem. Soc. 1996, 118, 3757. Wu, S.; Lee, S.; Beak, P. J. Am. Chem. Soc. 1996, 118, 715. Schlosser, M.; Limat, D. J. Am. Chem. Soc. 1995, 117, 12342. Voyer, N.; Roby, J. Tetrahedron Lett. 1995, 36, 6627. Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1991, 113, 9708.
8. For lithiation reactions of chiral benzylamine derivatives see: Zhang, P.; Gawley, R. E. Tetrahedron Lett. 1992, 33, 2945. Meyers, A. I.; Guiles, J.; Warmus, J. S.; Gonzalez, M. A. Tetrahedron Lett. 1991, 32, 5505. Huber, I. M. P.; Seebach D. Helv. Chim. Acta 1987, 67, 1944. For lithiation reactions of prochiral benzylamines in the presence of (-)-sparteine see: Park, Y. S.; Beak, P. J. Org. Chem. 1997, 62, 1574. Park, Y. S.; Boys, M. L.; Beak, P. J. Am. Chem. Soc. 1996, 118, 3757. Wu, S.; Lee, S.; Beak, P. J. Am. Chem. Soc. 1996, 118, 715. Schlosser, M.; Limat, D. J. Am. Chem. Soc. 1995, 117, 12342. Voyer, N.; Roby, J. Tetrahedron Lett. 1995, 36, 6627. Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1991, 113, 9708.
9. For lithiation reactions of chiral benzylamine derivatives see: Zhang, P.; Gawley, R. E. Tetrahedron Lett. 1992, 33, 2945. Meyers, A. I.; Guiles, J.; Warmus, J. S.; Gonzalez, M. A. Tetrahedron Lett. 1991, 32, 5505. Huber, I. M. P.; Seebach D. Helv. Chim. Acta 1987, 67, 1944. For lithiation reactions of prochiral benzylamines in the presence of (-)-sparteine see: Park, Y. S.; Beak, P. J. Org. Chem. 1997, 62, 1574. Park, Y. S.; Boys, M. L.; Beak, P. J. Am. Chem. Soc. 1996, 118, 3757. Wu, S.; Lee, S.; Beak, P. J. Am. Chem. Soc. 1996, 118, 715. Schlosser, M.; Limat, D. J. Am. Chem. Soc. 1995, 117, 12342. Voyer, N.; Roby, J. Tetrahedron Lett. 1995, 36, 6627. Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1991, 113, 9708.
10. Boche, G. ; Lohrenz, J. C. W.; Opel, A. in "Lithium Chemistry: A Theoretical and Experimental Overview", Sapse, A.-M.; Schleyer, P. v. R. Eds.; Wiley-Interscience: New York, 1995, pp. 195-226 and references cited therein.
11. Seebach, D.; Beck, A. K.; Studer, A. in Modern Synthetic Methods 1995, Vol. 7, Ernst, B.; Leumann, C. Eds.; VCH: Weinheim 1995, pp. 1-178.
12. Oshikawa, T.; Yamashita, M.; Kumagai, S.; Seo, K.; Kobayashi, J. J. Chem. Soc., Chem. Commun. 1995, 435. Alexakis, A.; Frutos, J. C.; Mutti, S.; Mangeney, P. J. Org. Chem. 1994, 59, 3326. Alexakis, A.; Mutti, S.; Mangeney, P. J. Org. Chem. 1992, 57, 1224.
13. Oshikawa, T.; Yamashita, M.; Kumagai, S.; Seo, K.; Kobayashi, J. J. Chem. Soc., Chem. Commun. 1995, 435. Alexakis, A.; Frutos, J. C.; Mutti, S.; Mangeney, P. J. Org. Chem. 1994, 59, 3326. Alexakis, A.; Mutti, S.; Mangeney, P. J. Org. Chem. 1992, 57, 1224.
14. Oshikawa, T.; Yamashita, M.; Kumagai, S.; Seo, K.; Kobayashi, J. J. Chem. Soc., Chem. Commun. 1995, 435. Alexakis, A.; Frutos, J. C.; Mutti, S.; Mangeney, P. J. Org. Chem. 1994, 59, 3326. Alexakis, A.; Mutti, S.; Mangeney, P. J. Org. Chem. 1992, 57, 1224.
15. Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 118, 6161.
16. However, achiral phosphoric triamides already have been lithiated and trapped with electrophiles: Savignac, P.; Leroux, Y.; Normant, H. Tetrahedron 1975, 31, 877. Normant, H.; Cuvigny, T.; Martin, G. J. Bull. Soc. Chim. Fr. 1969, 1605.
17. However, achiral phosphoric triamides already have been lithiated and trapped with electrophiles: Savignac, P.; Leroux, Y.; Normant, H. Tetrahedron 1975, 31, 877. Normant, H.; Cuvigny, T.; Martin, G. J. Bull. Soc. Chim. Fr. 1969, 1605.
18. -1.
19. +, (100).
20. The relative stereochemistry of 7 has been determined by X-ray structure analysis in our group. The R-configuration at the new stereogenic center has been assigned in relation to the (1R,2R) configuration of the bicyclic phosphoric diamide moiety.
21. The gas phase structures of lithiated phosphoric triamides have been calculated by ab initio methods in our group, a manuscript is in preparation.
22. The relative stereochemistry of the major product of 4 has been determined by comparison with the coupling product of the (1R,2R) phosphoric diamide 1 with (R)-N-methyl-1-phenylethyl amine to be (R,R,R).