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Synlett

Volumn , Issue 20, 2006, Pages 3389-3394

P-chirogenic α-carboxyphosphine boranes as effective pre-ligands in palladium-catalyzed asymmetric reactions

(4) Dolhem, Franck a Johansson, Magnus J a Antonsson, Thomas b Kann, Nina a

a CHALMERS UNIVERSITY OF TECHNOLOGY (Sweden)

b ASTRAZENECA R AND D (Sweden)

Author keywords

Allylic alkylation; Allylic amination; Asymmetric catalysis; P chiral; Phosphine ligands

Indexed keywords

ACETIC ACID; ALPHA CARBOXYPHOSPHINE BORANE DERIVATIVE; BENZYLAMINE; BORANE DERIVATIVE; CARBONIC ACID; DIMETHYLMALONATE; LIGAND; MALONIC ACID DERIVATIVE; PALLADIUM; SPARTEINE; UNCLASSIFIED DRUG;

ALKYLATION; AMINATION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOMER;

EID: 33846032956 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2006-956465 Document Type: Article

Times cited : (16)

References (49)

1
- 0031726658
- For some recent reviews on P-chirogenic phosphine ligands, see: a
- For some recent reviews on P-chirogenic phosphine ligands, see: (a) Ohff, M.; Holz, J.; Quirmbach, M.; Börner, A. Synthesis 1998, 1391.
- (1998) Synthesis , pp. 1391
- Ohff, M.¹ Holz, J.² Quirmbach, M.³ Börner, A.⁴

2
- 0041302599
- (b) Crépy, K. V. L.; Imamoto, T. Adv. Synth. Catal. 2003, 345, 79.
- (2003) Adv. Synth. Catal , vol.345 , pp. 79
- Crépy, K.V.L.¹ Imamoto, T.²

3
- 3843067342
- (c) Crépy, K. V. L.; Imamoto, T. Top. Curr. Chem. 2003, 229, 1.
- (2003) Top. Curr. Chem , vol.229 , pp. 1
- Crépy, K.V.L.¹ Imamoto, T.²

4
- 8144222270
- (d) Johansson, M. J.; Kann, N. C. Mini-Rev. Org. Chem. 2004, 1, 233.
- (2004) Mini-Rev. Org. Chem , vol.1 , pp. 233
- Johansson, M.J.¹ Kann, N.C.²

5
- 0025152027
- Jugé, S.; Stephan, M.; Laffitte, J. A.; Genêt, J. P. Tetrahedron Lett. 1990, 31, 6357.
- (1990) Tetrahedron Lett , vol.31 , pp. 6357
- Jugé, S.¹ Stephan, M.² Laffitte, J.A.³ Genêt, J.P.⁴

6
- 0000895308
- Muci, A. R.; Campos, K. R.; Evans, D. A. J. Am. Chem. Soc. 1995, 117, 9075.
- (1995) J. Am. Chem. Soc , vol.117 , pp. 9075
- Muci, A.R.¹ Campos, K.R.² Evans, D.A.³

7
- 0032572094
- (a) Wolfe, B.; Livinghouse, T. J. Am. Chem. Soc. 1998, 120, 5116.
- (1998) J. Am. Chem. Soc , vol.120 , pp. 5116
- Wolfe, B.¹ Livinghouse, T.²

8
- 0035189273
- (b) Heath, H.; Wolfe, B.; Livinghouse, T.; Bae, S. K. Synthesis 2001, 2341.
- (2001) Synthesis , pp. 2341
- Heath, H.¹ Wolfe, B.² Livinghouse, T.³ Bae, S.K.⁴

9
- 0042932780
- For some examples, see: a
- For some examples, see: (a) Hoge, G. J. Am. Chem. Soc. 2003, 125, 10219.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 10219
- Hoge, G.¹

10
- 14944379368
- (b) Liu, D.; Zhang, X. Eur. J. Org. Chem. 2005, 646.
- (2005) Eur. J. Org. Chem , pp. 646
- Liu, D.¹ Zhang, X.²

11
- 27644437671
- (c) Wiktelius, D.; Johansson, M. J.; Luthman, K.; Kann, N. Org. Lett. 2005, 7, 4991.
- (2005) Org. Lett , vol.7 , pp. 4991
- Wiktelius, D.¹ Johansson, M.J.² Luthman, K.³ Kann, N.⁴

12
- 0037048610
- (a) Dearden, M. J.; Firkin, C. R.; Hermet, J. P. R.; O'Brien, P. J. Am. Chem. Soc. 2002, 124, 11870.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 11870
- Dearden, M.J.¹ Firkin, C.R.² Hermet, J.P.R.³ O'Brien, P.⁴

13
- 0344084118
- (b) Hermet, J. P. R.; Porter, D. W.; Dearden, M. J.; Harrison, J. R.; Koplin, T.; O'Brien, P.; Parmene, J.; Tyurin, V.; Whitwood, A. C.; Gilday, J.; Smith, N. M. Org. Biomol. Chem. 2003, 1, 3977.
- (2003) Org. Biomol. Chem , vol.1 , pp. 3977
- Hermet, J.P.R.¹ Porter, D.W.² Dearden, M.J.³ Harrison, J.R.⁴ Koplin, T.⁵ O'Brien, P.⁶ Parmene, J.⁷ Tyurin, V.⁸ Whitwood, A.C.⁹ Gilday, J.¹⁰ Smith, N.M.¹¹

14
- 4043120293
- (c) Dearden, M. J.; McGrath, M. J.; O'Brien, P. J. Org. Chem. 2004, 69, 5789.
- (2004) J. Org. Chem , vol.69 , pp. 5789
- Dearden, M.J.¹ McGrath, M.J.² O'Brien, P.³

15
- 0034689851
- Maniere, E.; Rouden, J.; Tadino, V.; Lasne, M.-C. Org. Lett. 2000, 2, 1121.
- (2000) Org. Lett , vol.2 , pp. 1121
- Maniere, E.¹ Rouden, J.² Tadino, V.³ Lasne, M.-C.⁴

16
- 4043091525
- (a) Johansson, M. J.; Schwartz, L. O.; Amedjkouh, M.; Kann, N. C. Eur. J. Org. Chem. 2004, 1894.
- (2004) Eur. J. Org. Chem , pp. 1894
- Johansson, M.J.¹ Schwartz, L.O.² Amedjkouh, M.³ Kann, N.C.⁴

17
- 8144220434
- (b) Johansson, M. J.; Schwartz, L.; Amedjkouh, M.; Kann, N. Tetrahedron: Asymmetry 2004, 15, 3531.
- (2004) Tetrahedron: Asymmetry , vol.15 , pp. 3531
- Johansson, M.J.¹ Schwartz, L.² Amedjkouh, M.³ Kann, N.⁴

18
- 28444457008
- See also
- (c) See also: McGrath, M. J.; O'Brien, P. J. Am. Chem. Soc. 2005, 127, 16378.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 16378
- McGrath, M.J.¹ O'Brien, P.²

19
- 0035808963
- (a) Ohashi, A.; Imamoto, T. Tetrahedron Lett. 2001, 42, 1099.
- (2001) Tetrahedron Lett , vol.42 , pp. 1099
- Ohashi, A.¹ Imamoto, T.²

20
- 0036329765
- (b) Ohashi, A.; Kikuchi, S.; Yasutake, M.; Imamoto, T. Eur. J. Org. Chem. 2002, 2535.
- (2002) Eur. J. Org. Chem , pp. 2535
- Ohashi, A.¹ Kikuchi, S.² Yasutake, M.³ Imamoto, T.⁴

21
- 0346363688
- (c) Danjo, H.; Higuchi, M.; Yada, M.; Imamoto, T. Tetrahedron Lett. 2004, 45, 603.
- (2004) Tetrahedron Lett , vol.45 , pp. 603
- Danjo, H.¹ Higuchi, M.² Yada, M.³ Imamoto, T.⁴

22
- 0028895231
- See for example: a
- See for example: (a) Minami, T.; Okada, Y.; Otaguro, T.; Tawaraya, S.; Furuichi, T.; Okauchi, T. Tetrahedron: Asymmetry 1995, 6, 2469.
- (1995) Tetrahedron: Asymmetry , vol.6 , pp. 2469
- Minami, T.¹ Okada, Y.² Otaguro, T.³ Tawaraya, S.⁴ Furuichi, T.⁵ Okauchi, T.⁶

23
- 0034616326
- (b) Okauchi, T.; Fujita, K.; Ohtaguro, T.; Ohshima, S.; Minami, T. Tetrahedron: Asymmetry 2000, 11, 1397.
- (2000) Tetrahedron: Asymmetry , vol.11 , pp. 1397
- Okauchi, T.¹ Fujita, K.² Ohtaguro, T.³ Ohshima, S.⁴ Minami, T.⁵

24
- 0037530082
- (c) Ebran, J. P.; Jubault, P.; Pannecoucke, X.; Quirion, J. C. Tetrahedron: Asymmetry 2003, 14, 1637.
- (2003) Tetrahedron: Asymmetry , vol.14 , pp. 1637
- Ebran, J.P.¹ Jubault, P.² Pannecoucke, X.³ Quirion, J.C.⁴

25
- 27144447062
- Lam, H.; Horton, P. N.; Hursthouse, M. B.; Aldous, D. J.; Hu, K. K. Tetrahedron Lett. 2005, 46, 8145.
- (2005) Tetrahedron Lett , vol.46 , pp. 8145
- Lam, H.¹ Horton, P.N.² Hursthouse, M.B.³ Aldous, D.J.⁴ Hu, K.K.⁵

26
- 19944428910
- Sun, X. M.; Manabe, K.; Lam, W. W. L.; Shiraishi, N.; Kobayashi, J.; Shiro, M.; Utsumi, H.; Kobayashi, S. Chem. Eur. J. 2005, 11, 361.
- (2005) Chem. Eur. J , vol.11 , pp. 361
- Sun, X.M.¹ Manabe, K.² Lam, W.W.L.³ Shiraishi, N.⁴ Kobayashi, J.⁵ Shiro, M.⁶ Utsumi, H.⁷ Kobayashi, S.⁸

27
- 33846077719
- Compounds 2a,c,d,22 2b,23 2e24 and 2f3 were prepared as described in the literature. Compounds 2g and 2h were prepared via the corresponding phosphine sulfides using the same procedure as for 2f.3 Compound 2i was prepared from PCl3 and 2,4,6-tri(isopropyl)-1- phenylmagnesium bromide, following a literature procedure.25 P,P-Dimethyl(2-biphenyl)phosphine Sulfide (Precursor to 2g) Waxy solid; 89% yield; mp 99-101 °C. IR (KBr, ν, 2986, 2873, 1770, 1458, 1383, 1140 cm-1. 1H NMR (CDCl3, δ, 1.58 (d, J, 13.2 Hz, 6 H, 7.18-7.47 (m, 8 H, 8.20-8.27 (m, 1 H, 13C NMR (CDCl3, δ, 23.56 (d, J =56.9 Hz, 127.39 (d, J, 12.2 Hz, 127.87, 128.05, 129.54, 130.80 (d, J, 3.1 Hz, 131.23 (d, J, 9.1 Hz, 131.96 (d, J, 75.8 Hz, 132.23 d, J
- 32BP: C, 73.39; H, 11.59. Found: C, 73.31; H, 11.68.

28
- 33846080750
- Compounds 3a-d were prepared according the literature, 22.23 affording ligands of the following enantiopurity as determined by reduction to the corresponding alcohol: 3a (96, 3b (85, 3c (90, 3d (92, General Procedure for 3e-i To a solution of, )-sparteine or, )-1 (1.12 equiv) in anhyd Et2O (2.5 mL/mmol) under argon at -78 °C was added a 1.3 M solution (1.1 equiv) of sec-BuLi in hexane. The mixture was stirred for 30 min at -78 °C before the slow addition of a Et2O solution (3 mL/mmol) of the prochiral phosphine borane. The mixture was stirred at -78 °C for 3 h before CO2 was bubbled through the solution. The flask was slowly warmed up to r.t. over a period of 1 h and then acidified with 1 M HCl. The aqueous layer was extracted with EtOAc 3 ×, The pH of the combined organic layers was adjusted to pH 12 using sat. Na2CO3. After phase separation
- 3¶DMS, and then subjected to analysis by HPLC on a Chiralcel OD-H column, eluting with n-hexane-i-PrOH.

29
- 33846058038
- S, )-Mesityl(ethanoic acid)methylphosphine-borane (3e) Transparent gel; 90% yield. IR (KBr, ν, 3100, 2960, 2720, 2520, 2170, 1705, 1640, 1340, 1180, 995 cm-1. 1H NMR (CDCl 3, δ, 1.1 (m, 3 H, 1.88 (d, J, 9.2 Hz, 3 H, 2.24 (s, 3 H, 2.55 (s, 6 H, 2.98 (dd, J, 14.0, 9.6 Hz, 1 H, 3.18 (dd, J, 14.0, 9.6 Hz, 1 H, 6.85 (d, J, 3.2 Hz, 2 H, 10.96 (br s, 1 H, 13C NMR (CDCl3, δ, 15.9 (d, J, 39.5 Hz, 21.04 (s, 24.10 (d, J, 4.6 Hz, 35.61 (d, J, 27.3 Hz, 121.14 (d, J, 47.0 Hz, 131.38 (d, J, 9.1 Hz, 141.16 (d, J, 3.1 Hz, 143.26 (d, J, 9.9 Hz, 173.69 (d, J, 4.5 Hz, α]D21 -15.0 (c 1, CHCl3, 80% ee, Anal. Calcd for C12H20BO2P: C, 60.54; H, 8.47. Found: C, 60.28; H, 8.43. Retention times for alcohol 90% n-h
- 13C NMR (100 MHz, CDCl3:

30
- 33846093654
- 2P: C, 47.77; H, 6.14. Found: C, 47.86; H, 10.30.
- 2P: C, 47.77; H, 6.14. Found: C, 47.86; H, 10.30.

31
- 6844254916
- For a comprehensive review on this reaction, see: a
- For a comprehensive review on this reaction, see: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
- (1996) Chem. Rev , vol.96 , pp. 395
- Trost, B.M.¹ Van Vranken, D.L.²

32
- 0036371962
- For some more recent reviews, see: b
- For some more recent reviews, see: (b) Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1.
- (2002) Chem. Pharm. Bull , vol.50 , pp. 1
- Trost, B.M.¹

33
- 4344566130
- (c) Trost, B. M. J. Org. Chem. 2004, 69, 5813.
- (2004) J. Org. Chem , vol.69 , pp. 5813
- Trost, B.M.¹

34
- 20344375609
- de Meijere, A, Diederich, F, Eds, Wiley-VCH: Weinheim Germany, Chap. 9
- (d) Kazmaier, U.; Pohlman, M. In Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim Germany, 2004, Chap. 9.
- (2004) Metal-Catalyzed Cross-Coupling Reactions
- Kazmaier, U.¹ Pohlman, M.²

35
- 33846079377
- Beller, M, Bolm, C, Eds, Wiley-VCH: Weinheim, Chap. 2.14
- (e) Heumann, A. In Transition Metals for Organic Synthesis; Beller, M.; Bolm, C., Eds.; Wiley-VCH: Weinheim, 2004, Chap. 2.14.
- (2004) Transition Metals for Organic Synthesis
- Heumann, A.¹

36
- 0035896231
- For some mechanistic considerations, see
- (f) For some mechanistic considerations, see: Amatore, C.; Gamez, S.; Jutand, A. Chem. Eur. J. 2001, 7, 1273.
- (2001) Chem. Eur. J , vol.7 , pp. 1273
- Amatore, C.¹ Gamez, S.² Jutand, A.³

37
- 0001019938
- Darcel, C.; Kaloun, E. B.; Merdes, R.; Moulin, D.; Riegel, N.; Thorimbert, S.; Genêt, J. P.; Jugé, S. J. Organomet. Chem. 2001, 624, 333.
- (2001) J. Organomet. Chem , vol.624 , pp. 333
- Darcel, C.¹ Kaloun, E.B.² Merdes, R.³ Moulin, D.⁴ Riegel, N.⁵ Thorimbert, S.⁶ Genêt, J.P.⁷ Jugé, S.⁸

38
- 33846063962
- General Procedure for the Palladium-Catalyzed Allylic Asymmetric Alkylation Reactions. To the phosphine-borane (0.019 mmol, 9.5% mol) under an argon atmosphere was added an anhyd degassed solution of Pd(AcO)2 (2.3 mg, 5 mol, in 0.8 mL THF. This mixture was stirred at r.t. for 15 min whereupon 1,3-diphenylpropenyl acetate (5, 50 μL, 1 equiv) or 1,3-diphenylpropenyl ethylcarbonate (6, 56 μL, 1 equiv) was added. After 15 min at r.t, dimethylmalonate (70 μL, 3 equiv) and BSA (150 μL, 3 equiv) were successively added. The mixture was stirred at r.t. and the reaction was monitored by HPLC and TLC. The mixture was purified by flash chromatography on silica gel, eluting with PE-EtOAc 95:5. The enantiomeric excess was determined by chiral HPLC, Chiralpak AD-H, n-hexane-i-PrOH (9:1) 1 mL/min, 254 nm, retention time: tR (R, 9.60 min, tRS, 13.22 min
- R(S) = 13.22 min.

39
- 14844340658
- For some recent examples, see: a
- For some recent examples, see: (a) Faller, J. W.; Wilt, J. C. Org. Lett. 2005, 7, 633.
- (2005) Org. Lett , vol.7 , pp. 633
- Faller, J.W.¹ Wilt, J.C.²

40
- 27144508180
- (b) Faller, J. W.; Wilt, J. C. Organometallics 2005, 24, 5076.
- (2005) Organometallics , vol.24 , pp. 5076
- Faller, J.W.¹ Wilt, J.C.²

41
- 28244438103
- (c) Zheng, W.-H.; Sun, N.; Hou, X. L. Org. Lett. 2005, 7, 5151.
- (2005) Org. Lett , vol.7 , pp. 5151
- Zheng, W.-H.¹ Sun, N.² Hou, X.L.³

42
- 26444603763
- (d) Nemoto, T.; Masuda, T.; Akimoto, Y.; Fukuyama, T.; Hamada, Y. Org. Lett. 2005, 7, 4447.
- (2005) Org. Lett , vol.7 , pp. 4447
- Nemoto, T.¹ Masuda, T.² Akimoto, Y.³ Fukuyama, T.⁴ Hamada, Y.⁵

43
- 0842328408
- (e) Uozumi, Y.; Tanaka, H.; Shibatomi, K. Org. Lett. 2004, 6, 281.
- (2004) Org. Lett , vol.6 , pp. 281
- Uozumi, Y.¹ Tanaka, H.² Shibatomi, K.³

44
- 0037037905
- (f) Jin, M. J.; Kim, S. H.; Lee, S. J.; Kim, Y. M. Tetrahedron Lett. 2002, 43, 7409.
- (2002) Tetrahedron Lett , vol.43 , pp. 7409
- Jin, M.J.¹ Kim, S.H.² Lee, S.J.³ Kim, Y.M.⁴

45
- 33846115323
- General Procedure for the Palladium-Catalyzed Asymmetric Allylic Amination Reactions. To the phosphine-borane (0.019 mmol, 9.5 mol, evacuated and flushed with argon, was added an anhyd, degassed THF solution (0.8 mL) of Pd(OAc)2 (2.3 mg, 5 mol, This mixture was stirred at r.t for 15 min, followed by the addition of 1,3-diphenylpropenyl acetate (5, 50 μL, 1 equiv) or 1,3-diphenylpropenyl ethylcarbonate (6, 56 μL, 1 equiv, After 15 min the reaction was cooled to 5 °C and benzylamine (66 μL) was added. The mixture was stirred at 5 °C and monitored by HPLC and TLC. The mixture was purified by flash chromatography on silica gel, eluting with PE-EtOAc 95:5. The enantiomeric excess was determined by chiral HPLC, Chiralpak AD-H, n-hexane-i-PrOH (9:1) 0.35 mL/min, 254 nm, retention time: tR (S, 28.64 min, t R R, 33.92 min
- R (R) = 33.92 min.

46
- 0032564850
- Imamoto, T.; Watanabe, J.; Wada, Y.; Masuda, H.; Yamada, H.; Tsuruta, H.; Matsukawa, S.; Yamaguchi, K. J. Am. Chem. Soc. 1998, 120, 1635.
- (1998) J. Am. Chem. Soc , vol.120 , pp. 1635
- Imamoto, T.¹ Watanabe, J.² Wada, Y.³ Masuda, H.⁴ Yamada, H.⁵ Tsuruta, H.⁶ Matsukawa, S.⁷ Yamaguchi, K.⁸

47
- 0042699953
- Oohara, N.; Katagiri, K.; Imamoto, T. Tetrahedron: Asymmetry 2003, 14, 2171.
- (2003) Tetrahedron: Asymmetry , vol.14 , pp. 2171
- Oohara, N.¹ Katagiri, K.² Imamoto, T.³

48
- 0037178489
- Maienza, F.; Spindler, F.; Thommen, M.; Pugin, B.; Malan, C.; Mezzetti, A. J. Org. Chem. 2002, 67, 5239.
- (2002) J. Org. Chem , vol.67 , pp. 5239
- Maienza, F.¹ Spindler, F.² Thommen, M.³ Pugin, B.⁴ Malan, C.⁵ Mezzetti, A.⁶

49
- 0033617302
- Yamanoi, Y.; Imamoto, T. J. Org. Chem. 1999, 64, 2988.
- (1999) J. Org. Chem , vol.64 , pp. 2988
- Yamanoi, Y.¹ Imamoto, T.²

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