Novel Chiral Sulfur-Containing Ferrocenyl Ligands for Palladium-Catalyzed Asymmetric Allylic Substitution

Chirality

Volumn 16, Issue 1, 2004, Pages 10-12

  Nakamura, Shuichi ^a   Fukuzumi, Takeo ^a   Toru, Takeshi ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Allylic substitution; Enantioselective reaction; Ferrocene; P,S bidentate ligands; Sulfoxide

Indexed keywords

ALLYL COMPOUND; FERROCENE DERIVATIVE; LIGAND; PALLADIUM; SULFOXIDE; SULFUR;

ARTICLE; CATALYSIS; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0346122787     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.10300     Document Type: Article

References (35)

1. For reviews, see: (a) Trost BM, Lee C. Asymmetric allylic alkylation reactions. In: Ojima I, editor. Catalytic asymmetric synthesis, 2nd ed. New York: Wiley-VCH; 2000. p 593-649.
2. (b) Pfaltz A, Lautens M. Allylic substitution reactions. In: Jacobsen EN, Pfaltz A, Yamamoto H. editors. Comprehensive asymmetric catalysis. Heidelberg: Springer; 1999. p 833-884;
3. (c) Trost BM, Vranken V, David L. Asymmetric Transition metal-catalyzed allylic alkylations. Chem Rev 1996;96:395-422.
4. For P,S-bidentate ligands, see: (a) Selvakumar K, Valentini M, Pregosin PS, Albinati A. Chiral phosphito-thioether complexes of palladium(0). Comments on the Pd, Rh, and Ir Regio- and enantioselective allylic alkylations of PhCH:CHCH(OAc)R, R = H, Me, Et. Organometallics 1999;18:4591-4597.
5. (b) Evans DA, Campos KR, Tedrow JS, Michael FE, Gagné MR. Application of chiral mixed phosphorus/sulfur ligands to palladium-catalyzed allylic substitutions. J Am Chem Soc 2000;122:7905-7920.
6. (c) Yan YY, RajanBabu TV. Ligand tuning in asymmetric catalysis: mono- and bis-phospholanes for a prototypical Pd-catalyzed asymmetric allylation reaction. Org Lett 2000;2:199-202.
7. (d) Nakano H, Okuyama Y, Yanagida M, Hongo H. Palladium-catalyzed asymmetric allylic substitution reactions using new chiral phosphinooxathiane ligands. J Org Chem 2001;66:620-625.
8. (e) Sugama H, Saito H, Danjo H, Imamoto T. P-chirogenic phosphine/ sulfide hybrid ligands. Synthesis 2001;2348-2353.
9. (f) Nakano H, Suzuki Y, Kabuto C, Fujita R, Hongo H. Chiral phosphinooxathiane ligands for catalytic asymmetric Diels-Alder reaction. J Org Chem 2002;67:5011-5014.
10. (g) Priego J, Mancheño OG, Cabrera S, Arrayás G, Llamas T, Carretero JC. 1-Phosphino-2-sulfenylferrocenes: efficient ligands in enantioselective palladium-catalyzed allylic substitutions and ring opening of 7-oxabenzonorbornadienes. Chem Commun 2002;2512-2513.
11. For chiral sulfoxide ligands, see: (h) Hiroi K, Suzuki Y, Abe I. Organosulfur functionality as an alternative enantiocontrollable coordinating element in chiral phosphine ligands for palladium-catalyzed asymmetric allylic alkylations. Chem Lett 1999a;149-150.
12. For P,S-bidentate ligands having a ferrocene skeleton, see: (a) Albinati A, Pregosin PS, Wick K. A new P,S-chiral auxiliary derived from thioglucose. X-ray structure of a palladium 1,3-diphenylallyl complex with a strongly rotated allyl ligand. Organometallics 1996;15:2419- 2421.
13. (b) Spencer J, Gramlich V, Häusel R, Togni A. Synthesis of P,S,O-ligands incorporating a planar chiral ferrocenyl motif. Tetrahedron Asymmetry 1996;7:41-44.
14. (c) Kagan HB, Diter P, Gref A, Gullaneux D, Masson-Szymczak AM, Rebière F, Riant O, Samuel O, Taudien S. Towards new ferrocenyl ligands for asymmetric catalysis. Pure Appl Chem 1996;68:29-36.
15. (d) Chesney A, Bryce MR, Chubb RWJ, Batsanov AS, Howard JAK. Chiral ferrocenyl-oxazolines incorporating thioether units: effective ligands for palladium-catalyzed allylic substitution. Tetrahedron Asymmetry 1997;8:2337-2346.
16. (e) Enders D, Peters R, Lochtman R, Raabe G, Runsink J, Bats JW. Asymmetric synthesis of novel ferrocenyl ligands with planar and central chirality and their application to Pd-catalyzed allylic substitutions. Eur J Org Chem 2000;3399-3426.
17. For asymmetric reactions using sulfoxides as chiral ligands, see: (a) Carreño MC, Ruano JLG, Maestro MC, Cabrajas LMM. Catalytic activity of chiral βp-hydroxysulfoxides in the enantioselective addition of diethylzinc to benzaldehyde. Tetrahedron Asymmetry 1993;4:727-734.
18. (b) Chelucci G, Berta D, Saba A. Chiral sulfoxides and sulfides tethered to pyridines as ligands for enantioselective catalysis: palladium catalyzed allytic substitution and addition of diethylzinc to benzaldehyde. Tetrahedron 1997;53:3843-3848.
19. (c) Hiroi K, Suzuki Y, Kawagishi R. Chiral β-phosphino sulfoxides as chiral ligands in palladium-catalyzed asymmetric allylic nucleophilic substitution reactions. Tetrahedron Lett 1999b;40:715-718.
20. (d) Hiroi K, Suzuki Y, Abe I, Kawaguchi R. New chiral sulfoxide ligands possessing a phosphano or phosphanoamino functionality in palladium-catalyzed asymmetric allylic nucleophilic substitution reactions. Tetrahedron 2000;56:4701-4710.
21. (e) Hiroi K, Watanabe K, Abe I, Koseki M. New chiral sulfoxide ligands in catalytic asymmetric Diels-Alder reactions: double acceleration by the chiralities of the sulfoxides and oxazolines. Tetrahedron Lett 2001;42:7617-7619.
22. (f) Piego CJ, Mancheño OG. Cabrera S, Carretero JC. Amino-substituted 1-sulfinylferrocenes as chiral ligands in the addition of diethylzinc to aromatic aldehydes. J Org Chem 2002;67:1346-1353.
23. (g) Watanabe K, Hirasawa T, Hiroi K. Lewis acid-catalyzed asymmetric Diels-Alder reactions using chiral sulfoxide ligands: chiral 2-(arylsulfinylmethyl)-1,3-oxazoline derivatives. Chem Pharm Bull 2002;50:372-379.
24. Wright ME. 1,1′-Bis(tri-n-butylstannyl)ferrocene: selective transmetalation applied to the synthesis of new ferrocenyl ligands. Organometallics 1990;9:853-856.
25. Zhang W, Yoneda Y, Kida T, Nakatsuji Y, Ikeda I. Novel chiral P,N-ferrocene ligands in palladium-catalyzed asymmetric allylic alkylations. Tetrahedron Asymmetry 1998:9:3371-3380.
26. Recently, we reported an efficient method for the preparation of sulfinates: Watanabe Y, Mase N, Tateyama M, Toru T. An improved and efficient procedure for the preparation of chiral sulfinates from sulfonyl chloride using triphenylphosphine. Tetrahedron Asymmetry 1999;10:737-745.
27. Hiroi et al. (see Ref. 4d) reported that the optical purity of 2-phosphinylbenzene sulfoxides gradually decreases at room temperature by internal redox reaction between the sulfinyl and the phosphine groups. On the other hand, sulfoxides 3a-e were obtained without loss of optical purity.
28. Trost BM, Murphy DJ. A model for metal-templated catalytic asymmetric induction via π-allyl fragments. Organometallics 1985;4:1143-1145.
29. Leutenegger U, Umbricht G, Fahrni C, Matt P, Pfaltz A. 5-Azasemicorrins: a new class of bidentate nitrogen ligands for enantioselective catalysis. Tetrahedron 1992;48:2143-2156.
30. Vyskočil S, Smrčina M, Hanú V, Poláč ek M, Koěovsky P. Derivatives of 2-amino-2′ -diphenylphosphino-1,1′-binaphthyl (MAP) and their application in asymmetric palladium (0)-catalyzed allylic substitution. J Org Chem 1998;63:7738-7748.
31. 2-symmetric chiral bis-sulfoxide ligand and its palladium(II) complex. Tetrahedron Lett 1995;36:8035-8038; see also ref. 4d.
32. We did not take into account the conformational change around the Cp-Fe-Cp axis.
33. 3-Phenylallyl) (phosphanyloxazoline) palladium complexes: X-ray crystallographic studies, NMR investigations, and ab initio/DFT calculations. Chem Eur J 2002;8:3103-3114.
34. (a) Pfaltz A. Chiral semicorrins and related nitrogen heterocycles as ligands in asymmetric catalysis. Acc Chem Res 1993;26:339-345.
35. (b) Sprinz J, Kiefer M, Helmchen G, Reggelin M, Huttner G, Walter O, Zsolnai L. Catalysis of allylic substitutions by Pd complexes of oxazolines containing an additional P, S, or Se center. X-ray crystal structures and solution structures of chiral π-allyl palladium complexes of phosphinoaryloxazolines. Tetrahedron Lett 1994;35:1523-1526.