HØctor Fernµndez-PØrez et al.
COMMUNICATIONS
[5] a) R. Hoen, J. A. F. Boogers, H. Bernsmann, A. J. Min-
naard, A. Meetsma, T. D. Tiemersma-Wegman,
A. H. M. de Vries, J. G. de Vries, B. L. Feringa, Angew.
Chem. Int. Ed. 2005, 44, 4209–4212; b) C. Monti, C.
Gennari, U. Piarulli, J. G. de Vries, A. H. M. de Vries,
L. Lefort, Chem. Eur. J. 2005, 11, 6701–6717; c) M. T.
Reetz, X. Li, Angew. Chem. Int. Ed. 2005, 44, 2959–
2962; d) J. G. de Vries, L. Lefort, Chem. Eur. J. 2006,
12, 4722–4734.
[6] a) B. Breit, Angew. Chem. Int. Ed. 2005, 44, 6816–
6825; b) M. Weis, C. Waloch, W. Seiche, B. Breit, J.
Am. Chem. Soc. 2006, 128, 4188–4189; c) X.-B. Jiang,
L. Lefort, P. E. Goudriaan, A. H. M. de Vries,
P. W. N. M. van Leeuwen, J. G. de Vries, J. N. H. Reek,
Angew. Chem. Int. Ed. 2006, 45, 1223–1227; d) A. J.
Sandee, A. M. Van der Burg, J. N. H. Reek, Chem.
Commun. 2007, 864–866; e) G. Hattori, T. Hori, Y.
Miyake, Y. Nishibayashi, J. Am. Chem. Soc. 2007, 129,
12930–12931.
Perkin Trans. 1 1983, 989–994; c) D. Boeckh, R. Huis-
gen, H. Noeth, J. Am. Chem. Soc. 1987, 109, 1248–
1249; d) H. Brunner, A. Sicheneder, Angew. Chem.
1988, 100, 730–731; e) F. Gorla, A. Togni, L. M. Venan-
zi, A. Albinati, F. Lianza, Organometallics 1994, 13,
1607–1616.
[10] For the phosphorylation of hydroxy phosphines leading
to phosphine-phosphinites see for example: a) M. Ya-
mashita, K. Hiramatsu, M. Yamada, N. Suzuki, S. Ino-
kawa, Bull. Chem. Soc. Jpn. 1982, 55, 2917–2921; b) A.
Monsees, S. Laschat, Synlett 2002, 1011–1013; c) K.
Ohe, K. Morioka, K. Yonehara, S. Uemura, Tetrahe-
dron: Asymmetry 2002, 13, 2155–2160; d) X. Jia, X. Li,
W. S. Lam, S. H. L. Kok, L. Xu, G. Lu, C.-H. Yeung,
A. S. C. Chan, Tetrahedron: Asymmetry 2004, 15, 2273–
2278; e) Y. Yan, Y. Chi, X. Zhang, Tetrahedron: Asym-
metry 2004, 15, 2173–2175; f) N. Boyer, M. Leautey, P.
Jubault, X. Pannecoucke, J.-C. Quirion, Tetrahedron:
Asymmetry 2005, 16, 2455–2458.
[7] a) A. Vidal-Ferran, A. Moyano, M. A. Pericas, A.
Riera, J. Org. Chem. 1997, 62, 4970–4982; b) A. Vidal-
Ferran, N. Bampos, A. Moyano, M. A. Pericas, A.
Riera, J. K. M. Sanders, J. Org. Chem. 1998, 63, 6309–
6318; c) C. Puigjaner, A. Vidal-Ferran, A. Moyano,
M. A. Pericas, A. Riera, J. Org. Chem. 1999, 64, 7902–
7911; d) M. A. Pericas, C. Puigjaner, A. Riera, A.
Vidal-Ferran, M. Gomez, F. Jimenez, G. Muller, M.
Rocamora, Chem. Eur. J. 2002, 8, 4164–4178; e) D.
Popa, C. Puigjaner, M. Gomez, J. Benet-Buchholz, A.
Vidal-Ferran, M. A. Pericas, Adv. Synth. Catal. 2007,
349, 2265–2278.
[8] See for example: a) B. M. Trost, D. L. Van Vranken, C.
Bingel, J. Am. Chem. Soc. 1992, 114, 9327–9343;
b) T. V. Rajanbabu, A. L. Casalnuovo, T. A. Ayers,
Adv. Catal. Processes 1997, 2, 1–41; c) R. Kranich, K.
Eis, O. Geis, S. Muhle, J. W. Bats, H.-G. Schmalz,
Chem. Eur. J. 2000, 6, 2874–2894; d) S. J. Degrado, H.
Mizutani, A. H. Hoveyda, J. Am. Chem. Soc. 2001, 123,
755–756; e) Y. Hamashima, M. Kanai, M. Shibasaki,
Tetrahedron Lett. 2001, 42, 691–694; f) O. Pamies,
G. P. F. van Strijdonck, M. Dieguez, S. Deerenberg, G.
Net, A. Ruiz, C. Claver, P. C. J. Kamer, P. W. N. M. van
Leeuwen, J. Org. Chem. 2001, 66, 8867–8871; g) P. I.
Dalko, L. Moisan, J. Cossy, Angew. Chem. Int. Ed.
2002, 41, 625–628; h) M. Dieguez, A. Ruiz, C. Claver,
J. Org. Chem. 2002, 67, 3796–3801; i) M. Locatelli,
P. G. Cozzi, Angew. Chem. Int. Ed. 2003, 42, 4928–
4930; j) J. F. Jensen, I. Sotofte, H. O. Sorensen, M. Jo-
hannsen, J. Org. Chem. 2003, 68, 1258–1265; k) S.
Jeulin, S. D. De Paule, V. Ratovelomanana-Vidal, J.-P.
Genet, N. Champion, P. Dellis, Proc. Natl. Acad. Sci. U.
S. A. 2004, 101, 5799–5804; l) B. Goldfuss, T. Loesch-
mann, F. Rominger, Chem. Eur. J. 2004, 10, 5422–5431;
m) T. F. Knoepfel, P. Zarotti, T. Ichikawa, E. M. Car-
reira, J. Am. Chem. Soc. 2005, 127, 9682–9683; n) Y.
Liu, K. Ding, J. Am. Chem. Soc. 2005, 127, 10488–
10489; o) F. R. Leroux, H. Mettler, Adv. Synth. Catal.
2007, 349, 323–336; p) J. J. Miller, M. S. Sigman, J. Am.
Chem. Soc. 2007, 129, 2752–2753.
[11] For the phosphorylation of hydroxy phosphines leading
to phosphine-phosphites see for example refs.[10d,e] and
a) N. Sakai, S. Mano, K. Nozaki, H. Takaya, J. Am.
Chem. Soc. 1993, 115, 7033–7034; b) T. Horiuchi, T.
Ohta, E. Shirakawa, K. Nozaki, H. Takaya, J. Org.
Chem. 1997, 62, 4285–4292; c) K. Nozaki, N. Sakai, T.
Nanno, T. Higashijima, S. Mano, T. Horiuchi, H.
Takaya, J. Am. Chem. Soc. 1997, 119, 4413–4423; d) S.
Deerenberg, H. S. Schrekker, G. P. F. Van Strijdonck,
P. C. J. Kamer, P. W. N. M. Van Leeuwen, J. Fraanje, K.
Goubitz, J. Org. Chem. 2000, 65, 4810–4817; e) O.
Pamies, M. Dieguez, G. Net, A. Ruiz, C. Claver, Chem.
Commun. 2000, 2383–2384; f) S. Deerenberg, O.
Pamies, M. Dieguez, C. Claver, P. C. J. Kamer,
P. W. N. M. van Leeuwen, J. Org. Chem. 2001, 66,
7626–7631; g) A. Suarez, A. Pizzano, Tetrahedron:
Asymmetry 2001, 12, 2501–2504; h) F. Blume, S. Ze-
molka, T. Fey, R. Kranich, H.-G. Schmalz, Adv. Synth.
Catal. 2002, 344, 868–883; i) A. Suarez, M. A. Mendez-
Rojas, A. Pizzano, Organometallics 2002, 21, 4611–
4621; j) S. Vargas, M. Rubio, A. Suarez, D. Del Rio, E.
Alvarez, A. Pizzano, Organometallics 2006, 25, 961–
973.
[12] C. Jimeno, A. Vidal-Ferran, M. A. Pericas, Org. Lett.
2006, 8, 3895–3898.
[13] Methyl and trityl protecting groups can be regarded as
the two extremes in terms of steric congestion around
the CH2OR chain.
[14] Y. Gao, J. M. Klunder, R. M. Hanson, H. Masamune,
S. Y. Ko, K. B. Sharpless, J. Am. Chem. Soc. 1987, 109,
5765–5780.
[15] S. T. Cacatian, P. L. Fuchs, Tetrahedron 2003, 59, 7177–
7187.
[16] P-O-P ligands derived from 7c will be reported else-
where in due time.
[17] Chiral phosphites derived from BINOL are highly effi-
cient ligands in hydrogenation reactions. However, in
the cases reported by Reetz there is not such a big dif-
ference between the matched and mismatched cases as
in our case: M. T. Reetz, G. Mehler, Angew. Chem. Int.
Ed. 2000, 39, 3889–3890.
[9] a) K. Issleib, K. Rockstroh, Chem. Ber. 1963, 96, 407–
410; b) A. C. Connell, G. H. Whitham, J. Chem. Soc.
1990
ꢀ 2008 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2008, 350, 1984 – 1990