I. Sato, Y. Toyota, N. Asakura
SHORT COMMUNICATION
Conclusions
[
[
1] a) E. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.), Comprehensive
Asymmetric Catalysis, Springer, Heidelberg, 1999; b) I. Ojima
We developed mixed triarylbismuthanes and Me Zn rea-
2
(
Ed.), Catalytic Asymmetric Synthesis Second Edition, Wiley-
gents for the aryl transfer reaction to aromatic aldehydes in
the presence of chiral β-amino alcohol catalysts to give
highly enantiomerically enriched diarylmethanols in good
yield.
VCH, New York, 2000.
2] a) K. Soai, T. Kawasaki, I. Sato in The Chemistry of Organoz-
inc Compounds: The Chemistry of Functional Groups (Eds.: Z.
Rappoport, I. Marek), Wiley, Chichester, 2006, ch.12, pp. 555–
5
93; b) K. Soai, S. Niwa, Chem. Rev. 1992, 92, 833; c) R.
Noyori, M. Kitamura, Angew. Chem. Int. Ed. Engl. 1991, 30,
9; d) L. Pu, H.-B. Yu, Chem. Rev. 2001, 101, 757.
4
Experimental Section
[
[
3] Review: C. Bolm, J. P. Hildebrand, K. Muñiz, N. Hermanns,
Angew. Chem. Int. Ed. 2001, 40, 3284.
4] a) K. Soai, Y. Kawase, A. Oshio, J. Chem. Soc., Perkin Trans.
General Procedure for the Asymmetric Aryl Transfer Reaction to
Aldehydes withTriarylbismuthane/Me Zn Reagents: Under a nitro-
2
1
1991, 1613; b) J. L. dem Bussche-Hünnefeld, D. Seebach, Tet-
gen atmosphere, triarylbismuthane (2.4 mmol) was dissolved in dry
toluene (7 mL). Dimethylzinc (1.0 in hexane, 7.2 mmol) was
added to the solution, and the reaction mixture was heated at reflux
for 10 h. After the mixture was cooled to 0 °C, a solution of the
chiral catalyst (0.10 mmol) in toluene (1 mL) was added to the mix-
ture. After 15 min of stirring, the aldehyde (1.00 mmol) was added
to the mixture, and the mixture was stirred for 16 h at 0 °C. The
reaction was quenched by the addition of hydrochloric acid (1 ,
rahedron 1992, 48, 5719; c) P. I. Dosa, J. C. Ruble, G. C. Fu, J.
Org. Chem. 1997, 62, 444; d) D.-H. Ko, K.-H. Kim, D. Ha,
Org. Lett. 2002, 4, 3759; e) For addition to ketones, see: P. I.
Dosa, G. C. Fu, J. Am. Chem. Soc. 1998, 120, 445.
[5] a) C. Bolm, K. Muñiz, Chem. Commun. 1999, 1295; b) C.
Bolm, N. Hermanns, J. P. Hildebrand, K. Muñiz, Angew.
Chem. Int. Ed. 2000, 39, 3465; c) C. Bolm, M. Kesselgruber,
N. Hermanns, J. P. Hildebrand, G. Raabe, Angew. Chem. Int.
Ed. 2001, 40, 1488.
6] a) W.-S. Huang, L. Pu, J. Org. Chem. 1999, 64, 4222; b) W.-S.
Huang, Q.-S. Hu, L. Pu, J. Org. Chem. 1999, 64, 7940; c) W.-
S. Huang, L. Pu, Tetrahedron Lett. 2000, 41, 145.
1
0 mL). After the addition of saturated aqueous NaHCO
the mixture was filtered through celite and extracted with AcOEt.
The extract was dried with Na SO and concentrated under re-
3
(15 mL),
[
2
4
duced pressure. Purification of the residue by preparative silica gel
TLC produced the optically active secondary alcohol. The ee value
was determined by HPLC analysis on a column fitted with a chiral
stationary phase (Chiralcel OD-H, OB-H, or Chiralpak AD-H).
[7] a) C. Bolm, J. Rudolph, J. Am. Chem. Soc. 2002, 124, 14850;
b) J. Rudolf, N. Hermanns, C. Bolm, J. Org. Chem. 2004, 69,
3997.
[
8] a) J.-X. Ji, J. Wu, T. T.-L. Au-Yeung, C.-W. Yip, R. K. Haynes,
A. S. C. Chan, J. Org. Chem. 2005, 70, 1093; b) Z. Chai, X.-Y.
Liu, X.-Y. Wu, G. Zhao, Tetrahedron: Asymmetry 2006, 17,
2442; c) X. Wu, X. Liu, G. Zhao, Tetrahedron: Asymmetry
2005, 16, 2299; d) D. Castellnou, M. Fontes, C. Jimeno, D.
Font, L. Sola, X. Verdaguer, M. A. Pericas, Tetrahedron 2005,
Asymmetric Aryl Transfer Reaction to p-Bromobenzaldehyde (1c)
with a Mixed (Z)-2-Phenyl-1,3,2-dioxabismepin-4,7-dione (3) and
Me Zn Reagent: For details see Scheme 2. Under a nitrogen atmo-
2
sphere, diethylzinc (1.0 in hexane, 2.7 mmol) was added to the
suspension of (Z)-2-phenyl-1,3,2-dioxabismepin-4,7-dione (3,
61, 12111.
[
9] a) H. Suzuki, Y. Matano (Eds.), Organobismuth Chemistry, El-
sevier, Amsterdam, 2001; b) N. M. Leonard, L. C. Wieland,
R. S. Mohan, Tetrahedron 2002, 58, 8373.
360 mg, 0.90 mmol) in toluene (2.7 mL). The mixture was heated
at reflux for 6 h. After the mixture was cooled to 0 °C, a solution
of (R)-DPMPM (24.1 mg, 0.0900 mmol) and aldehyde 1c (55.5 mg,
[
[
10] K. Soai, S. Yokoyama, T. Hayasaka, J. Org. Chem. 1991, 56,
0.30 mmol) in toluene (2.7 mL) was added. The mixture was stirred
4264.
for 14 h at 0 °C. The reaction was quenched by the addition of
hydrochloric acid (1 , 5 mL). After the addition of saturated aque-
11] K. Soai, A. Ookawa, T. Kaba, K. Ogawa, J. Am. Chem. Soc.
1987, 109, 7111.
ous NaHCO
3
(10 mL), the mixture was filtered through celite and
and con-
[12] D. H. R. Barton, N. J. Bhatnagar, J. P. Finet, W. B. Motherwell,
extracted with AcOEt. The extract was dried with MgSO
4
Tetrahedron 1986, 42, 3111.
13] a) T. Nishikawa, Y. Yamamoto, N. Miyaura, Chem. Commun.
[
centrated under reduced pressure. Purification of the residue by
preparative silica gel TLC (benzene/AcOEt, 20:1) produced (R)-(4-
bromophenyl)phenylmethanol (2c) (57.3 mg, 0.22 mmol). The yield
was 73%, with an estimated ee value of 92%.
2
004, 1822; b) D. H. R. Barton, N. Ozbalik, M. Ramesh, Tetra-
hedron 1988, 44, 7385.
[
14] a) T. Huang, Y. Meng, S. Venkatraman, D. Wang, C.-J. Li, J.
Am. Chem. Soc. 2001, 123, 7451; b) S. Venkatraman, C.-J. Li,
Tetrahedron Lett. 2001, 42, 781.
Supporting Information (see footnote on the first page of this arti-
cle): Experimental details and characteristic data of diarylmeth-
anols 2 are described.
[15] J.-P. Finet, Chem. Rev. 1989, 89, 1487.
[
16] a) H. Suzuki, T. Murafuji, J. Chem. Soc., Chem. Commun.
1
992, 1143; b) G. Witting, A. Maercker, J. Organomet. Chem.
1
967, 8, 491.
[
[
17] H. Gilman, H. L. Yale, J. Am. Chem. Soc. 1950, 52, 8.
18] For Barbier-type reaction of Bi , see: M. Wada, K. Akiba, Tet-
Acknowledgments
0
rahedron Lett. 1985, 26, 4211.
This work was supported by a Grant-in-Aid for Scientific Research
from the Ministry of Education, Sports, Culture, Science and Tech-
nology and Kaneko-Narita grant from the Protein Research Foun-
dation.
[
19] A. Georgiades, H. P. Latscha, Z. Naturforsch., Teil B 1980, 35,
1000.
Received: March 9, 2007
Published Online: April 26, 2007
2610
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Eur. J. Org. Chem. 2007, 2608–2610