Chiral allylsilane additions to chiral N-Boc-α-amino aldehydes

Synlett

Volumn , Issue 1, 2000, Pages 37-40

  Dias, Luiz C ^a   Meira, Paulo R R ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

amino aldehydes; Chiral allylsilane; Dipeptide isosteres; Homoallylic alcohols; Oxazolidines

Indexed keywords

ALDEHYDE DERIVATIVE; AMINOALDEHYDE; SILANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033978057     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (28)

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14. 4 is instantaneous at -60°C, affording the corresponding allyltrichlorostannane; Dias, L.C.; Meira, P.R.R.; Ferreira, E. Org. Lett. 1999, 1, 1335-1338.
15. 4 reduction of the corresponding Weinreb amides: Fehrentz, J-A.; Castro, B. Synthesis 1983, 676; (R)-α-amino aldehydes: Saari, W. S.; Fisher, T. E. Synthesis 1990, 453.
16. 4 reduction of the corresponding Weinreb amides: Fehrentz, J-A.; Castro, B. Synthesis 1983, 676; (R)-α-amino aldehydes: Saari, W. S.; Fisher, T. E. Synthesis 1990, 453.
17. The starting aldehydes should be used freshly prepared. Attempts to purify aldehydes 3-6 by silica-gel chromatography resulted in partial racemization. Since the diastereoselectivity of the reactions of these aldehydes with allylsilane 4 depends on their enantiomeric purity, crude aldehydes were used in all of the studies described in the text. For optical stability studies of N-protected α-amino aldehydes, see: (a) Ito, A.; Takahashi, R.; Baba, Y. Chem Pharm. Bull. 1975, 23, 3081;
18. (b) Garner, P.; Park, J. M. J. Org. Chem. 1987, 52, 2361.
19. 4. For a review about optically active N-protected α-amino aldehydes in organic synthesis, see: Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149;
20. (b) Based on the fact that reactions of chiral allylsilanes are more diastereoselective than those of simple allyltrimethylsilane, the possibility exists that the minor isomer in the chiral allylsilane additions derives from aldehyde racemization. For a related paper, see: Panek, J. S.; Liu, P. Tetrahedron Lett. 1997, 38, 5127.
21. 1H NMR analysis of the corresponding acetonides, prepared by treating the homoallylic alcohols with PPTS in 2,2-dimethoxypropane.
22. 13C NMR, IR, MS, and HRMS spectral data.
23. Evans, D. A.; Coleman, P. J.; Dias, L. C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2737.
24. For a definition of matched and mismatched terms, see: Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R, Angew Chem., Int. Ed. Engl. 1985, 24, 1.
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26. b indicate that these protons are on opposite faces of the heterocyclic ring and therefore the oxazolidinone is derived from a 1,2-syn adduct: Kiyooka, S.; Nakano, M.; Shiota, F.; Fujiyama, R. J. Org. Chem. 1989, 54, 5409.
27. For related analysis of allyl-metal additions, see: Roush, W. R.; Palkowitz, A. D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 6348.
28. 4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel (30% EtOAc/hexanes) afforded the corresponding homoallylic alcohols.