LETTER
Synthesis of R-(-)-Muscone
1813
b) Sakane, S.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett.
1983, 24, 943. c) Tsuji, J.; Yamada, T.; Shimizu, I. J. Org.
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References and Notes
(1) a) Rossiter, B.E.; Swingle, N.M. Chem. Rev. 1992, 92, 771.
b) Krause, N. Angew. Chem. Int. Ed. Engl. 1997, 36, 187.
c) Alexakis, A. in Transition Metal Catalysed Reactions;
Murahashi, S.-I.; Davies, S.G. Ed.; IUPAC Blackwell
Science, Oxford, 1999; p 303.
(2) a) Villacorta, G.M.; Rao, C.P.; Lippard, S.J. J. Am. Chem. Soc.
1988, 110, 3182. b) Knotter, D.M.; Grove, D.M.; Smeets,
W.J.J.; Speck, A.L.; van Koten, G. J. Am. Chem. Soc. 1992,
114, 3400. c) Kanai, M.; Tomioka, K. Tetrahedron Lett. 1995,
36, 4273. d) Strangeland, E.L.; Sammakia, T. Tetrahedron
1997, 53, 16503.
(7) For recent asymmetric syntheses see : a) Kamat, V.P.;
Hagiwara, H.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin
Trans. I 1998, 2253. b) Yamaguchi, M.; Shiraishi, T.; Hirama,
M. J. Org. Chem. 1996, 61, 3520. c) Oppolzer, W.; Radinov,
R.N. J. Am. Chem. Soc. 1993, 115, 1593. d) Terunuma, D.;
Motegi, M.; Tsuda, M.; Sawada, T.; Nozawa, H.; Nohira, H.
J. Org. Chem. 1987, 52, 1630. e) Nelson, K.A.; Mash, E.A. J.
Org. Chem. 1986, 51, 2721.
(3) Alexakis, A.; Frutos, J.C.; Mangeney, P. Tetrahedron:
Asymmetry 1993, 4, 2427.
(8) Ogawa, T.; Fang, C.-L.; Suemune, H.; Sakai, K. Chem.
Commun. 1991, 1438.
(4) a) de Vries, A.H.M.; Meetsma, A.; Feringa, B.L. Angew.
Chem. Int. Ed. Engl. 1996, 35, 2374. b) de Vries, A.H.M.;
Hof, R.P.; Staal, D.; Kellog, R.M.; Feringa, B.L. Tetrahedron:
Asymmetry 1997, 8, 1539. c) Alexakis, A.; Vastra, J.; Burton,
J.; Mangeney, P. Tetrahedron: Asymmetry 1997, 8, 3193.
d) Alexakis, A.; Burton, J.; Vastra, J.; Mangeney, P.
Tetrahedron: Asymmetry 1997, 8, 3987. e) Feringa, B.L.;
Pineschi, M.; Arnold, L.A.; Imbos, R.; de Vries, A.H.M.
Angew. Chem. Int. Ed. Engl. 1997, 36, 2620. f) Knöbel,
A.K.H.; Escher, I.H.; Pfaltz, A. Synlett 1997, 1429. g) Zhang,
F.-Y.; Chan, A.S.C. . Tetrahedron: Asymmetry 1998, 9, 1179
h). Sewald, N.; Wendisch, V. Tetrahedron: Asymmetry 1998,
9, 1341. i) Keller, E.; Maurer, J.; Naasz, R.; Schader, T.;
Meetsma, A.; Feringa, B.L. Tetrahedron: Asymmetry 1998, 9,
2409. j) Alexakis, A.; Vastra, J.; Burton, J.; Benhaïm, C.;
Mangeney, P. Tetrahedron Lett. 1998, 39, 4821. k) Mori, T.;
Kosaka, K.; Nakagawa, Y.; Nagaoka, Y. Tomioka, K.
Tetrahedron: Asymmetry 1998, 9, 3175. l) Yan, M.; Yang, L.-
W.; Wong, K.-Y.; Chan, A.S.C. Chem. Commun. 1999, 11.
m) Yamanoi, Y.; Imamoto, T. J. Org. Chem. 1999, 64, 2988.
For a non-phosphorus ligand see : n) Bennett, S.M.W.;
Brown, S.M.; Muxworthy, J.P.; Woodward, S. Tetrahedron
Lett. 1999, 40, 1767. For a conjugate addition involving
RB(OH)2 and a chiral Rh-based catalyst see : o) Takaya, Y.;
Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am.
Chem. Soc. 1998, 120, 5579.
(9) a) Tanaka, K.; Ushio, H.; Suzuki, H. Chem. Com. 1990, 795.
b) Tanaka, K.; Ushio, H.; Kawabata, Y.; Suzuki, H. J. Chem.
Soc., Perkin Trans. I 1991, 1445. c) Tanaka, K.; Matsui, J.;
Suzuki, H. J. Chem. Soc., Perkin Trans. I 1993, 153.
(10) Typical procedure : A mixture of Cu(OTf)2 (3 mg, 0.0083
mmol), toluene (3 mL) and chiral ligand 9a (8 mg, 0.0166
mmol) was stirred for 30 min, at room temperature. After
cooling to -30°C, Et2Zn (1M sol. in hexanes, 1.2 mL, 1.2
mmol) was added followed by a solution of the enone (0.85
mmol) in toluene (3 mL). The reaction was followed by GC
until completion (1-3 h). Acidic work-up and silica gel
chromatography gave the pure adduct. The ee was determined
by chiral GC on a Chiraldex G-TA (30 x 0.25 mm) capillary
column. For R-(-)-muscone the procedure was the following :
A mixture of Cu(OTf)2 (3 mg, 0.0083 mmol), toluene (3 mL)
and chiral ligand 9a (8 mg, 0.0166 mmol) was stirred for 30
min, at room temperature. After cooling to -10°C, Me2Zn (2M
sol. in toluene, 0.29 mL, 0.58 mmol) was added followed by a
solution of enone 6 (90 mg, 0.4 mmol) in toluene (1 mL). The
reaction was followed by GC until completion (3 h). Acidic
work-up and silica gel chromatography gave 50 mg of R-(-)-
muscone, identical with an authentic sample kindly provided
by Firmenich S.A.
(5) For a review, see : Ohloff, G. Fortschr. Chem. Forsch. 1969,
12, 185.
(6) See among others : a) Kabbara, J.; Flemming, S.; Nickisch, K.;
Neh, H.; Westermann, J. Chem. Ber. 1994, 127, 1489.
Article Identifier:
1437-2096,E;1999,0,11,1811,1813,ftx,en;G19199ST.pdf
Synlett 1999, No. 11, 1811–1813 ISSN 0936-5214 © Thieme Stuttgart · New York