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Volumn 575, Issue 1, 1999, Pages 1-20

Use of organomanganese reagents in organic synthesis

Author keywords

Addition reaction; Bromine manganese exchange; Organomanganese reagents; Radical cyclization

Indexed keywords


EID: 0001884490     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(98)00967-X     Document Type: Review
Times cited : (62)

References (141)
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    • Cyclopropylborate has been also reported to undergo similar 1,2-migration
    • Cyclopropylborate has been also reported to undergo similar 1,2-migration: R.L. Danheiser, A.C. Savoca, J. Org. Chem. 50 (1985) 2401.
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    • and references cited therein
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    • 1-Alkylcyclopropylzincates have been reported to react with alkenyl halide in the presence of a Pd catalyst. See Ref. [3]
    • 1-Alkylcyclopropylzincates have been reported to react with alkenyl halide in the presence of a Pd catalyst. See Ref. [3].
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    • The reaction of 1,1-dibromoalkanes with trialkylzincate has been reported
    • The reaction of 1,1-dibromoalkanes with trialkylzincate has been reported. T. Harada, Y. Kotani, T. Katsuhira, A. Oku, Tetrahedron Lett. 32 (1991) 1573.
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    • Preparation of alkenylsilane: (a) Butterworth, London
    • Preparation of alkenylsilane: (a) E.W. Colvin, Silicon in Organic Synthesis, Butterworth, London, 1981, pp. 44-82. (b) W.P. Weber, Silicon Reagents for Organic Synthesis, Springer-Verlag, Berlin, 1983, pp. 79-113.
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    • (b) Springer-Verlag, Berlin
    • Preparation of alkenylsilane: (a) E.W. Colvin, Silicon in Organic Synthesis, Butterworth, London, 1981, pp. 44-82. (b) W.P. Weber, Silicon Reagents for Organic Synthesis, Springer-Verlag, Berlin, 1983, pp. 79-113.
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    • Decomposition of the dialkylmanganese species has been reported to proceed by α,β-elimination of an hydrido-manganese species They mentioned that secondary alkyl manganese has decomposed much more easily than primary one
    • Decomposition of the dialkylmanganese species has been reported to proceed by α,β-elimination of an hydrido-manganese species. H. Tamura, J. Kochi, J. Organomet. Chem. 29 (1971) 111. They mentioned that secondary alkyl manganese has decomposed much more easily than primary one.
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    • Tamura, H.1    Kochi, J.2
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    • Oxidative insertion of manganese into organic halides has been reported. (a)
    • Oxidative insertion of manganese into organic halides has been reported. (a) T. Hiyama, M. Obayashi, A. Nakamura, Organometallics 1 (1982) 1249. (b) S.-H. Kim, M.V. Hansen, R.D. Rieke, Tetrahedron Lett. 37 (1996) 2197. (c) A. Fürstner, H. Brunner, Tetrahedron Lett. 37 (1996) 7009. (d) K. Takai, T. Ueda, T. Hayashi, T. Moriwake, Tetrahedron Lett. 37 (1996) 7049.
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    • (b)
    • Oxidative insertion of manganese into organic halides has been reported. (a) T. Hiyama, M. Obayashi, A. Nakamura, Organometallics 1 (1982) 1249. (b) S.-H. Kim, M.V. Hansen, R.D. Rieke, Tetrahedron Lett. 37 (1996) 2197. (c) A. Fürstner, H. Brunner, Tetrahedron Lett. 37 (1996) 7009. (d) K. Takai, T. Ueda, T. Hayashi, T. Moriwake, Tetrahedron Lett. 37 (1996) 7049.
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    • Kim, S.-H.1    Hansen, M.V.2    Rieke, R.D.3
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    • (c)
    • Oxidative insertion of manganese into organic halides has been reported. (a) T. Hiyama, M. Obayashi, A. Nakamura, Organometallics 1 (1982) 1249. (b) S.-H. Kim, M.V. Hansen, R.D. Rieke, Tetrahedron Lett. 37 (1996) 2197. (c) A. Fürstner, H. Brunner, Tetrahedron Lett. 37 (1996) 7009. (d) K. Takai, T. Ueda, T. Hayashi, T. Moriwake, Tetrahedron Lett. 37 (1996) 7049.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7009
    • Fürstner, A.1    Brunner, H.2
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    • (d)
    • Oxidative insertion of manganese into organic halides has been reported. (a) T. Hiyama, M. Obayashi, A. Nakamura, Organometallics 1 (1982) 1249. (b) S.-H. Kim, M.V. Hansen, R.D. Rieke, Tetrahedron Lett. 37 (1996) 2197. (c) A. Fürstner, H. Brunner, Tetrahedron Lett. 37 (1996) 7009. (d) K. Takai, T. Ueda, T. Hayashi, T. Moriwake, Tetrahedron Lett. 37 (1996) 7049.
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    • Alkyl migration of α-haloborate: (a)
    • Alkyl migration of α-haloborate: (a) H.C. Brown, M.M. Rogic, H. Nambu, M.W. Rathke, J. Am. Chem. Soc. 91 (1969) 2147. (b) H.C. Brown, M.M. Rogic, M.W. Rathke, G.W. Kabalka, J. Am. Chem. Soc. 90 (1968) 1911. (c) H.C. Brown, H. Nambu, M.M. Rogic, J. Am. Chem. Soc. 91 (1969) 6852. (d) H.C. Brown, H. Nambu, M.M. Rogic, J. Am. Chem. Soc. 91 (1969) 6855. (e) H.C. Brown, M.M. Rogic, M.W. Rathke, G.W. Kabalka, J. Am. Chem. Soc. 90 (1968) 818.
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    • (b)
    • Alkyl migration of α-haloborate: (a) H.C. Brown, M.M. Rogic, H. Nambu, M.W. Rathke, J. Am. Chem. Soc. 91 (1969) 2147. (b) H.C. Brown, M.M. Rogic, M.W. Rathke, G.W. Kabalka, J. Am. Chem. Soc. 90 (1968) 1911. (c) H.C. Brown, H. Nambu, M.M. Rogic, J. Am. Chem. Soc. 91 (1969) 6852. (d) H.C. Brown, H. Nambu, M.M. Rogic, J. Am. Chem. Soc. 91 (1969) 6855. (e) H.C. Brown, M.M. Rogic, M.W. Rathke, G.W. Kabalka, J. Am. Chem. Soc. 90 (1968) 818.
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    • Brown, H.C.1    Rogic, M.M.2    Rathke, M.W.3    Kabalka, G.W.4
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    • (c)
    • Alkyl migration of α-haloborate: (a) H.C. Brown, M.M. Rogic, H. Nambu, M.W. Rathke, J. Am. Chem. Soc. 91 (1969) 2147. (b) H.C. Brown, M.M. Rogic, M.W. Rathke, G.W. Kabalka, J. Am. Chem. Soc. 90 (1968) 1911. (c) H.C. Brown, H. Nambu, M.M. Rogic, J. Am. Chem. Soc. 91 (1969) 6852. (d) H.C. Brown, H. Nambu, M.M. Rogic, J. Am. Chem. Soc. 91 (1969) 6855. (e) H.C. Brown, M.M. Rogic, M.W. Rathke, G.W. Kabalka, J. Am. Chem. Soc. 90 (1968) 818.
    • (1969) J. Am. Chem. Soc. , vol.91 , pp. 6852
    • Brown, H.C.1    Nambu, H.2    Rogic, M.M.3
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    • (d)
    • Alkyl migration of α-haloborate: (a) H.C. Brown, M.M. Rogic, H. Nambu, M.W. Rathke, J. Am. Chem. Soc. 91 (1969) 2147. (b) H.C. Brown, M.M. Rogic, M.W. Rathke, G.W. Kabalka, J. Am. Chem. Soc. 90 (1968) 1911. (c) H.C. Brown, H. Nambu, M.M. Rogic, J. Am. Chem. Soc. 91 (1969) 6852. (d) H.C. Brown, H. Nambu, M.M. Rogic, J. Am. Chem. Soc. 91 (1969) 6855. (e) H.C. Brown, M.M. Rogic, M.W. Rathke, G.W. Kabalka, J. Am. Chem. Soc. 90 (1968) 818.
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    • Brown, H.C.1    Nambu, H.2    Rogic, M.M.3
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    • (e)
    • Alkyl migration of α-haloborate: (a) H.C. Brown, M.M. Rogic, H. Nambu, M.W. Rathke, J. Am. Chem. Soc. 91 (1969) 2147. (b) H.C. Brown, M.M. Rogic, M.W. Rathke, G.W. Kabalka, J. Am. Chem. Soc. 90 (1968) 1911. (c) H.C. Brown, H. Nambu, M.M. Rogic, J. Am. Chem. Soc. 91 (1969) 6852. (d) H.C. Brown, H. Nambu, M.M. Rogic, J. Am. Chem. Soc. 91 (1969) 6855. (e) H.C. Brown, M.M. Rogic, M.W. Rathke, G.W. Kabalka, J. Am. Chem. Soc. 90 (1968) 818.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 818
    • Brown, H.C.1    Rogic, M.M.2    Rathke, M.W.3    Kabalka, G.W.4
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    • Very recently, generation of manganese enolates from α-acetoxycarbonyl compounds with tributylmanganate has been reported:
    • Very recently, generation of manganese enolates from α-acetoxycarbonyl compounds with tributylmanganate has been reported: M. Hojo, H. Harada, H. Ito, A. Hosomi, J. Am. Chem. Soc. 119 (1997) 5459. Other methods for the generation of manganese enolates are as follows. Deprotonation: G. Cahiez, B. Figadere, P. Clery, Tetrahedron Lett. 35 (1994) 3065. Transmetallation: G. Cahiez, B. Figadere, P. Clery, Tetrahedron Lett. 35 (1994) 3069. 1,4-Addition: G. Cahiez, M. Alami, Tetrahedron Lett. 30 (1989) 3541. K. Takai, T. Ueda, H. Kaihara, Y. Sunami, T. Moriwake, J. Org. Chem. 61 (1996) 8728.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 5459
    • Hojo, M.1    Harada, H.2    Ito, H.3    Hosomi, A.4
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    • Other methods for the generation of manganese enolates are as follows. Deprotonation
    • Very recently, generation of manganese enolates from α-acetoxycarbonyl compounds with tributylmanganate has been reported: M. Hojo, H. Harada, H. Ito, A. Hosomi, J. Am. Chem. Soc. 119 (1997) 5459. Other methods for the generation of manganese enolates are as follows. Deprotonation: G. Cahiez, B. Figadere, P. Clery, Tetrahedron Lett. 35 (1994) 3065. Transmetallation: G. Cahiez, B. Figadere, P. Clery, Tetrahedron Lett. 35 (1994) 3069. 1,4-Addition: G. Cahiez, M. Alami, Tetrahedron Lett. 30 (1989) 3541. K. Takai, T. Ueda, H. Kaihara, Y. Sunami, T. Moriwake, J. Org. Chem. 61 (1996) 8728.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 3065
    • Cahiez, G.1    Figadere, B.2    Clery, P.3
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    • Transmetallation
    • Very recently, generation of manganese enolates from α-acetoxycarbonyl compounds with tributylmanganate has been reported: M. Hojo, H. Harada, H. Ito, A. Hosomi, J. Am. Chem. Soc. 119 (1997) 5459. Other methods for the generation of manganese enolates are as follows. Deprotonation: G. Cahiez, B. Figadere, P. Clery, Tetrahedron Lett. 35 (1994) 3065. Transmetallation: G. Cahiez, B. Figadere, P. Clery, Tetrahedron Lett. 35 (1994) 3069. 1,4-Addition: G. Cahiez, M. Alami, Tetrahedron Lett. 30 (1989) 3541. K. Takai, T. Ueda, H. Kaihara, Y. Sunami, T. Moriwake, J. Org. Chem. 61 (1996) 8728.
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    • Cahiez, G.1    Figadere, B.2    Clery, P.3
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    • 1,4-Addition
    • Very recently, generation of manganese enolates from α-acetoxycarbonyl compounds with tributylmanganate has been reported: M. Hojo, H. Harada, H. Ito, A. Hosomi, J. Am. Chem. Soc. 119 (1997) 5459. Other methods for the generation of manganese enolates are as follows. Deprotonation: G. Cahiez, B. Figadere, P. Clery, Tetrahedron Lett. 35 (1994) 3065. Transmetallation: G. Cahiez, B. Figadere, P. Clery, Tetrahedron Lett. 35 (1994) 3069. 1,4-Addition: G. Cahiez, M. Alami, Tetrahedron Lett. 30 (1989) 3541. K. Takai, T. Ueda, H. Kaihara, Y. Sunami, T. Moriwake, J. Org. Chem. 61 (1996) 8728.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 3541
    • Cahiez, G.1    Alami, M.2
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    • K. Takai, T. Ueda, H. Kaihara, Y. Sunami, T. Moriwake
    • Very recently, generation of manganese enolates from α-acetoxycarbonyl compounds with tributylmanganate has been reported: M. Hojo, H. Harada, H. Ito, A. Hosomi, J. Am. Chem. Soc. 119 (1997) 5459. Other methods for the generation of manganese enolates are as follows. Deprotonation: G. Cahiez, B. Figadere, P. Clery, Tetrahedron Lett. 35 (1994) 3065. Transmetallation: G. Cahiez, B. Figadere, P. Clery, Tetrahedron Lett. 35 (1994) 3069. 1,4-Addition: G. Cahiez, M. Alami, Tetrahedron Lett. 30 (1989) 3541. K. Takai, T. Ueda, H. Kaihara, Y. Sunami, T. Moriwake, J. Org. Chem. 61 (1996) 8728.
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    • From α-silyl amide: (a)
    • From α-silyl amide: (a) R.P. Woodbury, M.W. Rathke, J. Org. Chem. 42 (1977) 1688. (b) R.P. Woodbury, M.W. Rathke, J. Org. Chem. 43 (1978) 1947. (c) Peterson elimination reaction: D.J. Ager, Organic Reactions, vol. 38, Wiley, New York, 1990, pp. 1-223.
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    • From α-silyl amide: (a) R.P. Woodbury, M.W. Rathke, J. Org. Chem. 42 (1977) 1688. (b) R.P. Woodbury, M.W. Rathke, J. Org. Chem. 43 (1978) 1947. (c) Peterson elimination reaction: D.J. Ager, Organic Reactions, vol. 38, Wiley, New York, 1990, pp. 1-223.
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    • From α-silyl amide: (a) R.P. Woodbury, M.W. Rathke, J. Org. Chem. 42 (1977) 1688. (b) R.P. Woodbury, M.W. Rathke, J. Org. Chem. 43 (1978) 1947. (c) Peterson elimination reaction: D.J. Ager, Organic Reactions, vol. 38, Wiley, New York, 1990, pp. 1-223.
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    • Enolate of β-lactam: (a) F. DiNinno, T.R. Beattie, B.G. Christensen, J. Org. Chem. 42 (1977) 2960. (b) J.A. Aimetti, M.S. Kellogg, Tetrahedron Lett. (1979) 3805. (c) A. Martel, J.-P. Daris, C. Bachand, M. Menard, Can. J. Chem. 65 (1987) 2179.
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    • (b)
    • Enolate of β-lactam: (a) F. DiNinno, T.R. Beattie, B.G. Christensen, J. Org. Chem. 42 (1977) 2960. (b) J.A. Aimetti, M.S. Kellogg, Tetrahedron Lett. (1979) 3805. (c) A. Martel, J.-P. Daris, C. Bachand, M. Menard, Can. J. Chem. 65 (1987) 2179.
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    • Enolate of β-lactam: (a) F. DiNinno, T.R. Beattie, B.G. Christensen, J. Org. Chem. 42 (1977) 2960. (b) J.A. Aimetti, M.S. Kellogg, Tetrahedron Lett. (1979) 3805. (c) A. Martel, J.-P. Daris, C. Bachand, M. Menard, Can. J. Chem. 65 (1987) 2179.
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    • Reduced lactam, 1,4-diphenyl-2-azetidinone, was also obtained in 27% yield as a byproduct
    • Reduced lactam, 1,4-diphenyl-2-azetidinone, was also obtained in 27% yield as a byproduct.
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    • (g) G. Boisvert, R. Giasson
    • (g) G. Boisvert, R. Giasson, Tetrahedron Lett. 33 (1992) 6587.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 6587
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    • J. Iqbal, B. Bhatia, N.K. Nayyar, Chem. Rev. 94 (1994) 519. Palladium-catalyzed cyclization: (a) R.C. Larock, D.E. Stinn, Tetrahedron Lett. 29 (1988) 4687. (b) R.C. Larock, S. Babu, Tetrahedron Lett. 28 (1987) 5291. (c) R.C. Larock, D.E. Stinn, Tetrahedron Lett. 30 (1989) 2767. (d) L.S. Hegedus, Angew. Chem. Int. Ed. Engl. 27 (1988) 1113. (e) T. Sakamoto, Y. Kondo, H. Yamanaka, Heterocycles, 27 (1988) 2225. Nickel: (a) M. Mori, S. Kudo, Y. Ban, J. Chem. Soc. Perkin Trans. I (1978) 771. (b) S. Olivero, J.C. Clinet, E. Dunach, Tetrahedron Lett. 36 (1995) 4429. Cobalt: G. Pattenden, Chem. Soc. Rev. 17 (1988) 361. Zn-Mn: E. Riguet, I. Klement, C.K. Reddy, G. Cahiez, P. Knochel, Tetrahedron Lett. 37 (1996) 5865. Zn-Ni: A. Vaupel, P. Knochel, J. Org. Chem. 61 (1996) 5743.
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    • Palladium-catalyzed cyclization: (a)
    • J. Iqbal, B. Bhatia, N.K. Nayyar, Chem. Rev. 94 (1994) 519. Palladium-catalyzed cyclization: (a) R.C. Larock, D.E. Stinn, Tetrahedron Lett. 29 (1988) 4687. (b) R.C. Larock, S. Babu, Tetrahedron Lett. 28 (1987) 5291. (c) R.C. Larock, D.E. Stinn, Tetrahedron Lett. 30 (1989) 2767. (d) L.S. Hegedus, Angew. Chem. Int. Ed. Engl. 27 (1988) 1113. (e) T. Sakamoto, Y. Kondo, H. Yamanaka, Heterocycles, 27 (1988) 2225. Nickel: (a) M. Mori, S. Kudo, Y. Ban, J. Chem. Soc. Perkin Trans. I (1978) 771. (b) S. Olivero, J.C. Clinet, E. Dunach, Tetrahedron Lett. 36 (1995) 4429. Cobalt: G. Pattenden, Chem. Soc. Rev. 17 (1988) 361. Zn-Mn: E. Riguet, I. Klement, C.K. Reddy, G. Cahiez, P. Knochel, Tetrahedron Lett. 37 (1996) 5865. Zn-Ni: A. Vaupel, P. Knochel, J. Org. Chem. 61 (1996) 5743.
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    • 3MnLi
    • 3MnLi.
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    • Decomposition of the dialkylmanganese species has been reported. See Ref. [12]
    • Decomposition of the dialkylmanganese species has been reported. See Ref. [12].
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    • An alternative mechanism, an iodine-manganese exchange followed by anionic carbomanganation giving 44, could not be negated. A more detailed study is obviously necessary to conclude the mechanism
    • An alternative mechanism, an iodine-manganese exchange followed by anionic carbomanganation giving 44, could not be negated. A more detailed study is obviously necessary to conclude the mechanism.
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    • Examples of sequences: (1) radical cyclization, (2) reduction to an organometallic, and (3) electrophilic trapping: (a)
    • Examples of sequences: (1) radical cyclization, (2) reduction to an organometallic, and (3) electrophilic trapping: (a) W.A. Nugent, T.V. RajanBabu, J. Am. Chem. Soc. 110 (1988) 8561. (b) K. Takai, K. Nitta, O. Fujimura, K. Utimoto, J. Org. Chem. 54 (1989) 4732. (c) See Ref. [27].
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    • Nugent, W.A.1    Rajanbabu, T.V.2
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    • (b)
    • Examples of sequences: (1) radical cyclization, (2) reduction to an organometallic, and (3) electrophilic trapping: (a) W.A. Nugent, T.V. RajanBabu, J. Am. Chem. Soc. 110 (1988) 8561. (b) K. Takai, K. Nitta, O. Fujimura, K. Utimoto, J. Org. Chem. 54 (1989) 4732. (c) See Ref. [27].
    • (1989) J. Org. Chem. , vol.54 , pp. 4732
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    • 2 afforded only the reduced product, phenyl prenyl ether, or N,N-diprenylaniline in 20 or 30% yield along with the recovered starting materials.
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    • Recently nickel or cobalt-catalyzed radical cyclization reaction has been reported. (a) A. Vaupel, P. Knochel, Tetrahedron Lett. 35 (1994) 8349. (b) T. Bamhaoud, J. Prandi, J. Chem. Soc. Chem. Commun. (1996) 1229.
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    • 3SiMgMe. The addition of PhCHO to the reagent provided only phenyl(trimethylsilyl)carbinol and no trace of 1-phenylethanol.
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    • 3MnMgBr is an active species in a catalytic reaction.
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    • 4CH(OH)Ph were detected in the reaction mixture.
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    • Recently a conjugate addition of the allylic copper species has been reported. B.H. Lipshutz, C. Hackmann, J. Org. Chem. 59 (1994) 7437.
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    • Further examples of the addition of other allylic organometallic reagents to alkynes are as follows. Allylic aluminum reagents: (a) J.A. Miller, E. Negishi, Tetrahedron Lett. 25 (1984) 5863. (b) E. Negishi, T. Takahashi, Synthesis (1988) 1. Allylic indium reagents: S. Araki, A. Imai, K. Shimizu, Y. Butsugan, Tetrahedron Lett. 33 (1992) 2581. Allylic boron reagents: (a) B.M. Mikhailov, Pure Appl. Chem. 39 (1974) 505. (b) B.M. Mikhailov, Organomet. Chem. Rev. 8[A] (1972) 1.
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    • Further examples of the addition of other allylic organometallic reagents to alkynes are as follows. Allylic aluminum reagents: (a) J.A. Miller, E. Negishi, Tetrahedron Lett. 25 (1984) 5863. (b) E. Negishi, T. Takahashi, Synthesis (1988) 1. Allylic indium reagents: S. Araki, A. Imai, K. Shimizu, Y. Butsugan, Tetrahedron Lett. 33 (1992) 2581. Allylic boron reagents: (a) B.M. Mikhailov, Pure Appl. Chem. 39 (1974) 505. (b) B.M. Mikhailov, Organomet. Chem. Rev. 8[A] (1972) 1.
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    • Further examples of the addition of other allylic organometallic reagents to alkynes are as follows. Allylic aluminum reagents: (a) J.A. Miller, E. Negishi, Tetrahedron Lett. 25 (1984) 5863. (b) E. Negishi, T. Takahashi, Synthesis (1988) 1. Allylic indium reagents: S. Araki, A. Imai, K. Shimizu, Y. Butsugan, Tetrahedron Lett. 33 (1992) 2581. Allylic boron reagents: (a) B.M. Mikhailov, Pure Appl. Chem. 39 (1974) 505. (b) B.M. Mikhailov, Organomet. Chem. Rev. 8[A] (1972) 1.
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    • Further examples of the addition of other allylic organometallic reagents to alkynes are as follows. Allylic aluminum reagents: (a) J.A. Miller, E. Negishi, Tetrahedron Lett. 25 (1984) 5863. (b) E. Negishi, T. Takahashi, Synthesis (1988) 1. Allylic indium reagents: S. Araki, A. Imai, K. Shimizu, Y. Butsugan, Tetrahedron Lett. 33 (1992) 2581. Allylic boron reagents: (a) B.M. Mikhailov, Pure Appl. Chem. 39 (1974) 505. (b) B.M. Mikhailov, Organomet. Chem. Rev. 8[A] (1972) 1.
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    • An allylic manganese reagent derived from allylic bromide and Mn(0) has been reported to react with aldehydes, providing homoallylic alcohols. (a)
    • An allylic manganese reagent derived from allylic bromide and Mn(0) has been reported to react with aldehydes, providing homoallylic alcohols. (a) T. Hiyama, M. Obayashi, A. Nakamura, Organometallics 1 (1982) 1249. (b) K. Takai, T. Ueda, T. Hayashi, T. Moriwake, Tetrahedron Lett. 37 (1996) 7049. (c) A. Fürstner, H. Brunner, Tetrahedron Lett. 37 (1996) 7009.
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    • An allylic manganese reagent derived from allylic bromide and Mn(0) has been reported to react with aldehydes, providing homoallylic alcohols. (a) T. Hiyama, M. Obayashi, A. Nakamura, Organometallics 1 (1982) 1249. (b) K. Takai, T. Ueda, T. Hayashi, T. Moriwake, Tetrahedron Lett. 37 (1996) 7049. (c) A. Fürstner, H. Brunner, Tetrahedron Lett. 37 (1996) 7009.
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    • An allylic manganese reagent derived from allylic bromide and Mn(0) has been reported to react with aldehydes, providing homoallylic alcohols. (a) T. Hiyama, M. Obayashi, A. Nakamura, Organometallics 1 (1982) 1249. (b) K. Takai, T. Ueda, T. Hayashi, T. Moriwake, Tetrahedron Lett. 37 (1996) 7049. (c) A. Fürstner, H. Brunner, Tetrahedron Lett. 37 (1996) 7009.
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    • 4] have been reported. R.J. Morris, G.S. Girolami, Organometallics 8 (1989) 1478. Cahiez et al. have reported the reaction of tetrafurylmanganate
    • 4] have been reported. R.J. Morris, G.S. Girolami, Organometallics 8 (1989) 1478. Cahiez et al. have reported the reaction of tetrafurylmanganate. G. Cahiez, P.-Y. Chavant, E. Metais, Tetrahedron Lett. 33 (1992) 5245.
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    • Cahiez, G.1    Chavant, P.-Y.2    Metais, E.3
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    • 2, ether was used because of its solubility
    • 2, ether was used because of its solubility.


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