Diphenylsilyldiethylene- (DPSide-) group: A new primary amine protection

Tetrahedron Letters

Volumn 40, Issue 29, 1999, Pages 5333-5336

  Kim, B Moon ^a   Cho, Jong Hyun ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID; AMINE; ESTER; ETHYLENE DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTECTION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033575505     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00970-3     Document Type: Article

References (18)

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2. a) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley: New York, 1991; b) Kocienski, P. J. Protecting Groups; Geoug Thieme Verlag Stuttgart: New York, 1994.
3. For the definition of "orthognoality" in protecting groups, see reference 1b, pp. 2-3.
4. For cyclic disilazane, see: Djuric, S.; Venit, J.; Magnus, P. Tetrahedron Lett. 1981, 22, 1787.
5. For a preparation through a slightly different route, see: Buell, G. R.; Corriu, R.; Guerin, C.; Spialter, L. J. Am. Chem. Soc. 1970, 92, 7424.
6. a) Brown, H. C.; Knights, E. F.; Scouten, C. G. J. Am. Chem. Soc. 1974, 96, 7765; b) Soderquist, J. A.; Brown, H. C. J. Org. Chem. 1980, 45, 3571.
7. a) Brown, H. C.; Knights, E. F.; Scouten, C. G. J. Am. Chem. Soc. 1974, 96, 7765; b) Soderquist, J. A.; Brown, H. C. J. Org. Chem. 1980, 45, 3571.
8. 3) δ 134.99, 134.68, 129.23, 127.99, 59.32, 18.05.
9. 3) δ 144.56, 134.38, 132.20, 132.07, 130.08, 129.73, 128.22, 127.63, 68.05, 21.48, 14.72.
10. 2Si 507.2468, found 507.2458.
11. 13C NMR, IR, and low and high resolution mass spectroscopic data for the indicated structures.
12. 2O, see: Krapcho, A. P.; Kuell, C. S. Synth. Commun. 1990, 20, 2559; (b) For selective Cbz protection of diamines, see: Atwell, G. J.; Denny, W. A. Synthesis 1984, 1032; (c) For phthalimide protection, see: Soine, T. O.; Buchdahl, M. R. Org. Syn. Coll. Vol. IV, 106.
13. 2O, see: Krapcho, A. P.; Kuell, C. S. Synth. Commun. 1990, 20, 2559; (b) For selective Cbz protection of diamines, see: Atwell, G. J.; Denny, W. A. Synthesis 1984, 1032; (c) For phthalimide protection, see: Soine, T. O.; Buchdahl, M. R. Org. Syn. Coll. Vol. IV, 106.
14. 2O, see: Krapcho, A. P.; Kuell, C. S. Synth. Commun. 1990, 20, 2559; (b) For selective Cbz protection of diamines, see: Atwell, G. J.; Denny, W. A. Synthesis 1984, 1032; (c) For phthalimide protection, see: Soine, T. O.; Buchdahl, M. R. Org. Syn. Coll. Vol. IV, 106.
15. Carpino, L. A.; Tsao, J.-H.; Ringsdorf, H.; Fell, E.; Hettrich, G. J. Chem. Soc., Chem. Commun. 1978, 358.
16. a) Boehm, T. L.; Showalter, H. D. H. J. Org. Chem. 1996, 61, 6498; b) Kessar, S. V.; Singh, P.; Kaur, N. P.; Chawla, U.; Shukla, K.; Aggarwal, P.; Venugopal, D. J. Org. Chem. 1991, 56, 3908; c) Johnson, C.R.; Tait, B. D. J. Org. Chem. 1987, 52, 281.
17. a) Boehm, T. L.; Showalter, H. D. H. J. Org. Chem. 1996, 61, 6498; b) Kessar, S. V.; Singh, P.; Kaur, N. P.; Chawla, U.; Shukla, K.; Aggarwal, P.; Venugopal, D. J. Org. Chem. 1991, 56, 3908; c) Johnson, C.R.; Tait, B. D. J. Org. Chem. 1987, 52, 281.
18. a) Boehm, T. L.; Showalter, H. D. H. J. Org. Chem. 1996, 61, 6498; b) Kessar, S. V.; Singh, P.; Kaur, N. P.; Chawla, U.; Shukla, K.; Aggarwal, P.; Venugopal, D. J. Org. Chem. 1991, 56, 3908; c) Johnson, C.R.; Tait, B. D. J. Org. Chem. 1987, 52, 281.