110, 2366; (c) S. Ma, Acc. Chem. Res., 2009, 42, 1679; (d) S. Ma,
Aldrichimica Acta, 2007, 40, 91; (e) S. Ma, Chem. Rev., 2005, 105,
2829; (f) B. M. Trost, Acc. Chem. Res., 2002, 35, 695;
(g) R. Zimmer, C. U. Dinesh, E. Nandann and F. A. Khan, Chem.
Rev., 2000, 100, 3067.
4 (a) S.-H. Kim, S.-J. Oh, Y. Kim and C.-M. Yu, Chem. Commun.,
2007, 5025; (b) C.-M. Yu, J. Youn and J. Jung, Angew. Chem., Int.
Ed., 2006, 45, 1553; (c) C.-M. Yu, J. Youn and H.-K. Jung, Bull.
Korean Chem. Soc., 2006, 27, 463; (d) C.-M. Yu, J. Youn and
M.-K. Lee, Org. Lett., 2005, 7, 3733; (e) C.-M. Yu, Y.-T. Hong and
J. Lee, J. Org. Chem., 2004, 69, 8506; (f) S. Kang, Y.-T. Hong,
J.-H. Lee, W.-Y. Kim, I. Lee and C.-M. Yu, Org. Lett., 2003, 5,
2813.
5 S.-H. Kim, S.-J. Oh, P.-S. Ho, S.-C. Kang, K.-J. O and C.-M. Yu,
Org. Lett., 2008, 10, 265.
6 (a) C.-M. Yu, C. Kim and J.-H. Kweon, Chem. Commun., 2004,
2494; (b) C.-M. Yu, S.-K. Yoon, K. Baek and J.-Y. Lee, Angew.
Chem., Int. Ed., 1998, 37, 2392.
7 Synthesis of axially chiral allenes, see review: M. Ogasawara,
Tetrahedron: Asymmetry, 2009, 20, 259.
Scheme 3 A plausible stereochemical and reaction route.
8 Reviews: (a) S. E. Denmark and J. Fu, Chem. Rev., 2003, 103, 2763;
(b) S. E. Denmark and N. G. Almstead, in Modern Carbonyl
Chemistry, ed. J. Otera, Wiley-VCH, Weinheim, 2000, p. 299;
(c) S. R. Chemler and W. R. Roush, in Modern Carbonyl Chemistry,
ed. J. Otera, Wiley-VCH, Weinheim, 2000, p. 403; (d) J. A. Marshall,
Chem. Rev., 2000, 100, 3163.
9 (a) R. W. Hoffmann, Angew. Chem., Int. Ed. Engl., 1982, 21, 555;
(b) W. R. Roush, A. E. Walts and L. K. Hoong, J. Am. Chem. Soc.,
1985, 107, 8186; (c) H. C. Brown and K. S. Bhat, J. Am. Chem.
Soc., 1986, 108, 293; (d) K. Smith, in Organometallics in Synthesis,
ed. M. Schlosser, Wiley, New York, 1994, p. 461; and also see
ref. 8b,c.
10 (a) E. Negishi and T. Yoshida, Chem. Commun., 1973, 606;
(b) N. Guennouni, C. Rasset-Deloge, B. Carboni and
M. Vaultier, Synlett, 1992, 581; (c) A. Kamabuchi, N. Miyaura
and A. Suzuki, Tetrahedron Lett., 1993, 34, 4827; (d) J. Renaud,
C.-D. Graf and L. Oberer, Angew. Chem., Int. Ed., 2000, 39, 3103;
(e) F. Carreaux, F. Posseme, B. Carboni, A. Arrieta, B. Lecea and
F. P. Cossio, J. Org. Chem., 2002, 67, 9153; (f) A. Botvinik, A. A.
A. Quntar, A. Rubinstein and M. Srebnik, J. Organomet. Chem.,
2009, 694, 3349.
Scheme 4 Synthesis of natural product 8.
respectively.17 Hydrogenation of 7b with Pd/C at 0 1C in
EtOAc provided 8 in 88% yield (Scheme 4).
11 J. R. Gonzalez, A. Z. Gonzalez and J. A. Soderquist, J. Am. Chem.
Soc., 2009, 131, 9924.
In summary, this communication describes an asymmetric
homoallenylboration of aldehydes through the intermolecular
allylic transfer reaction, which promises to be synthetically
useful. This transformation involves the formation of
2-dienylborane from chirally modified bromoborane with
homoallenyl tin reagent, and subsequently the intermolecular
allylic transfer reaction with aldehydes. Further studies
including synthetic applications and extension of this method
with substituted 2-boryldienes are in progress.
12 V. Coeffard, M. Aylward and P. J. Guiry, Angew. Chem., Int. Ed.,
2009, 48, 9152.
13 (a) E. J. Corey, C.-M. Yu and S. S. Kim, J. Am. Chem. Soc., 1989,
111, 5495; (b) E. J. Corey, C.-M. Yu and D.-H. Lee, J. Am. Chem.
Soc., 1990, 112, 878.
14 C.-M. Yu, S.-J. Lee and M. Jeon, J. Chem. Soc., Perkin Trans. 1,
1999, 3557.
15 Recent synthetic applications of homoallenyl alcohols:
(a) R. W. Bates and Y. Lu, Org. Lett., 2010, 12, 3938;
(b) B. Alcaide, P. Almendros, R. Carrascosa and T. Martinez del
Campo, Chem.–Eur. J., 2009, 15, 2496; (c) X. Cheng, X. Jiang,
Y. Yu and S. Ma, J. Org. Chem., 2008, 73, 8960.
Generous financial support from the National Research
Foundation (KRF-2006-312-C00234, R01-2007-000-20315-0
and NRF-2009-0076852) is gratefully acknowledged.
16 (a) K. Mori, in The Total Synthesis of Natural Products, vol. 9,
ed. J. ApSimon, John Wiley & Sons, New York, 1992, p. 220;
(b) J.-H. Yang, G.-C. Yang, C.-F. Lu and Z.-X. Chen, Tetrahedron:
Asymmetry, 2008, 19, 2164; (c) W. Qi and M. C. Mcintosh, Org.
Lett., 2008, 10, 357; (d) P. H. G. Zarbin, A. R. M. Oliveira,
F. Simonelli, J. A. F. P. Villar and O. Delay Jr, Tetrahedron Lett.,
2004, 45, 7399; (e) M. Sato, J.-i. Sakai, Y. Sugita, T. Nakano and
C. Kaneko, Tetrahedron Lett., 1990, 31, 7463; (f) R. Bernardi and
D. Ghiringhelli, Synthesis, 1989, 938.
Notes and references
1 General discussions, see: A. Hoffmann-Roder and N. Krause,
¨
Angew. Chem., Int. Ed., 2004, 43, 1196.
2 Modern Allene Chemistry, vol. 1, 2, ed. N. Krause and A. S. K.
Hashmi, Wiley-VCH, Weinheim, 2004.
¨
3 Selected reviews, see: (a) N. Krause, O. Aksin-Artok, V. Breker,
17 (a) E. Yoneda, T. Kaneko, S.-W. Zhang, K. Onitsuka and
S. Takahashi, Org. Lett., 2000, 2, 441; (b) S.-K. Kang,
K.-J. Kim, C.-M. Yu, J.-W. Hwang and Y.-K. Do, Org. Lett.,
2001, 3, 2851.
C. Deutsch, B. Gockel, M. Poonoth, Y. Sawama, Y. Sawama,
T. Sun and C. Winter, Pure Appl. Chem., 2010, 82, 1529;
(b) F. Denes, A. Perez-Luna and F. Chemla, Chem. Rev., 2010,
c
This journal is The Royal Society of Chemistry 2011
Chem. Commun., 2011, 47, 3811–3813 3813