Catalytic, enantioselective alkylations of N,O-acetals

Journal of Organic Chemistry

Volumn 64, Issue 7, 1999, Pages 2168-2169

  Ferraris, Dana ^a   Dudding, Travis ^a   Young, Brandon ^a   Drury III, William J ^a   Lectka, Thomas ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; ENANTIOMER; ORGANIC CHEMISTRY; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0033515594     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982421t     Document Type: Article

References (30)

1. For reviews, see: Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 477-511. (b) Mukaiyama, T.; Murakami, M. Synthesis 1987, 1043-1054.
2. For reviews, see: Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 477-511. (b) Mukaiyama, T.; Murakami, M. Synthesis 1987, 1043-1054.
3. For mechanistic work on alkylation of acetals: (c) Sammakia, T.; Smith, R. S. J. Am. Chem. Soc. 1994, 116, 7915-7916.
4. (d) Sammakia, T.; Smith, R. S. J. Am. Chem. Soc. 1992, 114, 10998-10999.
5. Hoveyda et al. have developed a Ni-catalyzed alkylation reaction of allylic acetals as formal equivalents for conjugate addition reactions: (a) Gomez-Bengoa, E.; Heron, N. M.; Didiuk, M. T.; Luchaco, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 7649-7650.
6. For reviews of achiral α-amidoalkylation reactions, see: (b) Zaugg, H. E. Synthesis 1984, 85-110.
7. Zaugg, H. E. Synthesis 1984, 181-212.
8. For amido alkylation using stoichiometric quantities of Lewis acid, see: (d) Mooiweer, H. H.; Ettema, K. W. A.; Hiemstra, H.; Spekamp, W. N. Tetrahedron 1990, 46, 2991-2998.
9. (e) Renaud, P.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1986, 25, 843-844.
10. (f) Shono, T.; Matsumura, Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1175.
11. Our recent work has focused on the use of chiral, transition metalphosphine complexes 2 to catalyze the addition of carbon-based nucleophiles 4 to imino esters 3 (X = Ts) with high diastereo- and enantioselectivity to yield protected amino acids 5: (a) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548-4549.
12. (b) Ferraris, D.; Young, B.; Cox, C.; Drury, W. J., III; Dudding, T.; Lectka, T. J. Org. Chem. 1998, 63, 6090-6091.
13. (c) Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006-11007. The drawbacks of this synthetic methodology are the purification and hydrolytic lability of the imine 3 as well as the deprotection of the tosyl group after alkylation.
14. Williams, R. M. Synthesis of Optically Active a-Amino Acids; Pergamon: New York, 1989.
15. Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 51, 5773-5776.
16. 4 and the solvent removed in vacuo. The crude residue (200 mg) was subjected to column chromatography on silica gel to yield 128 mg of the final product (93% yield, 95% ee).
17. Li, G.; Sharpless, K. B. Acta Chem. Scand. 1996, 50, 649-651.
18. Fujino, M.; Wakimasu, M.; Kitada, C. Chem. Pharm. Bull. 1981, 10, 2825-2831.
19. Bowman, W. R.; Coghlan, D. R. Tetrahedron 1997, 53, 15787-15798.
20. (a) Garigipati, R. S.; Tschaen, D. M.; Weinreb, S. M. J. Am. Chem. Soc. 1990, 112, 3475-3482.
21. (b) Weinreb, S. M.; Demko, D. M.; Lessen, T. A. Tetrahedron Lett. 1986, 42, 2099-2103.
22. Narayanan, B. A.; Bunnelle, W. H. Tetrahedron Lett. 1987, 28, 6261-6264.
23. All deprotection products 6a were converted to L-benzoylalanine upon acidic hydrolysis. The hydrolysis products were identical in every way to the literature compound; see: Gulobev, A. S.; Sewald, N.; Burger, K. Tetrahedron 1996, 52, 14757-14776. See Supporting Information for details
24. (a) Botting, N. P. Chem. Rev. 1995, 95, 1-412.
25. (b) Pellicciari, R.; Natalini, B.; Constantino, G. J. Med. Chem. 1994, 37, 647-655.
26. (a) Kita, Y.; Shibata, N.; Miki, T.; Takemura, Y.; Tamura, O. Chem. Pharm, Bull. 1992, 40(1), 12-20.
27. (b) Onaka, M.; Ohno, R.; Izumi, Y. Tetrahedron Lett. 1989, 30, 747-750.
28. See the Supporting Information for details.
29. Imine 3 has been fully characterized by Wienreb et al.: Tschaen, D. M.; Turos, E.; Weinreb, S. M. J. Org. Chem. 1984, 49, 5058-5064.
30. For acid-catalyzed siloxane formation, see: Grubb, W. T. J. Am. Chem. Soc. 1954, 76, 3408-3414.