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1
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0034746687
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For recent reviews on olefin metathesis, see: a) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043; c) R. Roy, S. K. Das, Chem. Commun. 2000, 519-529; d) A. J. Philips, A. D. Abell, Aldrichimica Acta 1999, 32, 75-90; e) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388; f) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; g) K. J. Ivin, J. Mol. Catal. A 1998, 133, 1-16; h) Alkene Metathesis in Organic Synthesis (Ed.: A. Fürstner), Springer, Berlin, 1998; i) M. L. Randall, M. L. Snapper, J. Mol. Catal. A 1998, 133, 29-40; j) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055.
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For recent reviews on olefin metathesis, see: a) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043; c) R. Roy, S. K. Das, Chem. Commun. 2000, 519-529; d) A. J. Philips, A. D. Abell, Aldrichimica Acta 1999, 32, 75-90; e) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388; f) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; g) K. J. Ivin, J. Mol. Catal. A 1998, 133, 1-16; h) Alkene Metathesis in Organic Synthesis (Ed.: A. Fürstner), Springer, Berlin, 1998; i) M. L. Randall, M. L. Snapper, J. Mol. Catal. A 1998, 133, 29-40; j) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055.
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For recent reviews on olefin metathesis, see: a) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043; c) R. Roy, S. K. Das, Chem. Commun. 2000, 519-529; d) A. J. Philips, A. D. Abell, Aldrichimica Acta 1999, 32, 75-90; e) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388; f) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; g) K. J. Ivin, J. Mol. Catal. A 1998, 133, 1-16; h) Alkene Metathesis in Organic Synthesis (Ed.: A. Fürstner), Springer, Berlin, 1998; i) M. L. Randall, M. L. Snapper, J. Mol. Catal. A 1998, 133, 29-40; j) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055.
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For recent reviews on olefin metathesis, see: a) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043; c) R. Roy, S. K. Das, Chem. Commun. 2000, 519-529; d) A. J. Philips, A. D. Abell, Aldrichimica Acta 1999, 32, 75-90; e) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388; f) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; g) K. J. Ivin, J. Mol. Catal. A 1998, 133, 1-16; h) Alkene Metathesis in Organic Synthesis (Ed.: A. Fürstner), Springer, Berlin, 1998; i) M. L. Randall, M. L. Snapper, J. Mol. Catal. A 1998, 133, 29-40; j) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055.
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For recent reviews on olefin metathesis, see: a) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043; c) R. Roy, S. K. Das, Chem. Commun. 2000, 519-529; d) A. J. Philips, A. D. Abell, Aldrichimica Acta 1999, 32, 75-90; e) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388; f) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; g) K. J. Ivin, J. Mol. Catal. A 1998, 133, 1-16; h) Alkene Metathesis in Organic Synthesis (Ed.: A. Fürstner), Springer, Berlin, 1998; i) M. L. Randall, M. L. Snapper, J. Mol. Catal. A 1998, 133, 29-40; j) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055.
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For recent reviews on olefin metathesis, see: a) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043; c) R. Roy, S. K. Das, Chem. Commun. 2000, 519-529; d) A. J. Philips, A. D. Abell, Aldrichimica Acta 1999, 32, 75-90; e) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388; f) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; g) K. J. Ivin, J. Mol. Catal. A 1998, 133, 1-16; h) Alkene Metathesis in Organic Synthesis (Ed.: A. Fürstner), Springer, Berlin, 1998; i) M. L. Randall, M. L. Snapper, J. Mol. Catal. A 1998, 133, 29-40; j) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055.
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For recent reviews on olefin metathesis, see: a) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043; c) R. Roy, S. K. Das, Chem. Commun. 2000, 519-529; d) A. J. Philips, A. D. Abell, Aldrichimica Acta 1999, 32, 75-90; e) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388; f) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; g) K. J. Ivin, J. Mol. Catal. A 1998, 133, 1-16; h) Alkene Metathesis in Organic Synthesis (Ed.: A. Fürstner), Springer, Berlin, 1998; i) M. L. Randall, M. L. Snapper, J. Mol. Catal. A 1998, 133, 29-40; j) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055.
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For recent reviews on olefin metathesis, see: a) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043; c) R. Roy, S. K. Das, Chem. Commun. 2000, 519-529; d) A. J. Philips, A. D. Abell, Aldrichimica Acta 1999, 32, 75-90; e) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388; f) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; g) K. J. Ivin, J. Mol. Catal. A 1998, 133, 1-16; h) Alkene Metathesis in Organic Synthesis (Ed.: A. Fürstner), Springer, Berlin, 1998; i) M. L. Randall, M. L. Snapper, J. Mol. Catal. A 1998, 133, 29-40; j) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055.
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For recent reviews on olefin metathesis, see: a) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043; c) R. Roy, S. K. Das, Chem. Commun. 2000, 519-529; d) A. J. Philips, A. D. Abell, Aldrichimica Acta 1999, 32, 75-90; e) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388; f) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; g) K. J. Ivin, J. Mol. Catal. A 1998, 133, 1-16; h) Alkene Metathesis in Organic Synthesis (Ed.: A. Fürstner), Springer, Berlin, 1998; i) M. L. Randall, M. L. Snapper, J. Mol. Catal. A 1998, 133, 29-40; j) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055.
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For recent reviews on olefin metathesis, see: a) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29; b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043; c) R. Roy, S. K. Das, Chem. Commun. 2000, 519-529; d) A. J. Philips, A. D. Abell, Aldrichimica Acta 1999, 32, 75-90; e) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388; f) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; g) K. J. Ivin, J. Mol. Catal. A 1998, 133, 1-16; h) Alkene Metathesis in Organic Synthesis (Ed.: A. Fürstner), Springer, Berlin, 1998; i) M. L. Randall, M. L. Snapper, J. Mol. Catal. A 1998, 133, 29-40; j) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055.
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R. H. Grubbs, H. E. Blackwell, D. J. O'Leary, R. A. Washenfelder, K. Miura, Tetrahedron Lett. 1999, 40, 1091-1094.
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0034639441
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R. H. Grubbs, H. E. Blackwell, A. K. Chatterjee, D. J. O'Leary, R. A. Washenfelder, D. A. Bussmann, J. Am. Chem. Soc. 2000, 122, 58-71.
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For the extension of this methodology to include one-pot CM/allylboration reactions, see: S. D. Goldberg, R. H. Grubbs, Angew. Chem. 2002, 114, 835-838; Angew. Chem. Int. Ed. 2002, 41, 807-810.
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0036495555
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For the extension of this methodology to include one-pot CM/allylboration reactions, see: S. D. Goldberg, R. H. Grubbs, Angew. Chem. 2002, 114, 835-838; Angew. Chem. Int. Ed. 2002, 41, 807-810.
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34
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0000681082
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For background information on the roles of methylidene and alkylidene intermediates derived from 6 in metathesis, see: R. H. Grubbs, M. Ulman, Organometallics 1998, 17, 2484-2489.
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Organometallics
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A. K. Chatterjee, D. P. Sanders, R. H. Grubbs, Org. Lett. 2002, 4, 1939-1942.
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A. K. Chatterjee, J. P. Morgan, M. Scholl, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 3783-3784.
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47
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85007628511
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note
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[32]
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48
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0037868773
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A. K. Chatterjee, R. H. Grubbs, Angew. Chem. 2002, 114, 3304-3306; Angew. Chem. Int. Ed. 2002, 41, 3171-3174.
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Angew. Chem.
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A. K. Chatterjee, R. H. Grubbs, Angew. Chem. 2002, 114, 3304-3306; Angew. Chem. Int. Ed. 2002, 41, 3171-3174.
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Angew. Chem. Int. Ed.
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J. Louie, C. W. Bielawski, R. H. Grubbs, J. Am. Chem. Soc. 2001, 123, 11312-11313.
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J. Am. Chem. Soc.
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Louie, J.1
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T.-L. Choi, A. K. Chatterjee, R. H. Grubbs, Angew. Chem. 2001, 113, 1317-1319; Angew. Chem. Int. Ed. 2001, 40, 1277-1279.
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For a similar example (see above) using water-soluble vinylidene and allenylidene complexes, see: M. Saoud, A. Romerosa, M. Peruzzini, Organometallics 2000, 19, 4005-4007.
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In this report the E/Z ratio was erroneously reversed
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Enyne metathesis with ethylene catalyzed by 6 was recently applied in the synthesis of natural products: a) M. Mori, K. Tonogaki, N. Nishiguchi, J. Org. Chem. 2002, 67, 224-226; b) S. Rodríguez-Conesa, P. Candal, C. Jiménez, J. Rodríguez, Tetrahedron Lett. 2001, 42, 6699-6702.
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Enyne metathesis with ethylene catalyzed by 6 was recently applied in the synthesis of natural products: a) M. Mori, K. Tonogaki, N. Nishiguchi, J. Org. Chem. 2002, 67, 224-226; b) S. Rodríguez-Conesa, P. Candal, C. Jiménez, J. Rodríguez, Tetrahedron Lett. 2001, 42, 6699-6702.
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85007640198
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note
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The butadiene products from these reactions can also be used in nickel-catalyzed [4+4] cycloadditions; see: reference [102].
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For an early example of RCM-mediated cleavage from a solid support, see: J.-U. Peters, S. Blechert, Synlett 1997, 348-350.
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Peters, J.-U.1
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For an example of RCM-mediated cleavage in carbohydrate synthesis, see: L. Knerr, R. R. Schmidt, Synlett 1999, 11, 1802-1804.
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175
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Complex 155 is the immobilized version of 1, the first active NHC catalyst; for background literature on the development of this system, see: a) L. Ackermann, A. Fürstner, T. Weskamp, F. J. Kohl, W. A. Herrmann, Tetrahedron Lett. 1999, 40, 4787-4790; b) J. Huang, E. D. Stevens, S. P. Nolan, J. L. Pedersen, J. Am. Chem. Soc. 1999, 121, 2674-2678; c) M. Scholl, T. M. Trnka, J. P. Morgan, R. H. Grubbs, Tetrahedron Lett. 1999, 40, 2247-2250.
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Complex 155 is the immobilized version of 1, the first active NHC catalyst; for background literature on the development of this system, see: a) L. Ackermann, A. Fürstner, T. Weskamp, F. J. Kohl, W. A. Herrmann, Tetrahedron Lett. 1999, 40, 4787-4790; b) J. Huang, E. D. Stevens, S. P. Nolan, J. L. Pedersen, J. Am. Chem. Soc. 1999, 121, 2674-2678; c) M. Scholl, T. M. Trnka, J. P. Morgan, R. H. Grubbs, Tetrahedron Lett. 1999, 40, 2247-2250.
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S. C. Schürer, S. Gessler, N. Buschmann, S. Blechert, Angew. Chem. 2000, 112, 4062-4065; Angew. Chem. Int. Ed. 2000, 39, 3898-3901.
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182
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4243081008
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Grubbs has prepared water-soluble catalysts that promote living ROMP and RCM reactions in aqueous and methanolic solutions (these species were not CM-active); for details of this pioneering work, see: a) B. Mohr, D. M. Lynn; R. H. Grubbs, Organometallics 1996, 15, 4317-4325; b) D. M. Lynn, B. Mohr, L. M. Henling, M. W. Day, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 6601-6609; c) D. M. Lynn, B. Mohr, R. H. Grubbs, J. Am. Chem. Soc. 1998, 120, 1627-1628; d) T. A. Kirkland, D. M. Lynn, R. H. Grubbs, J. Org. Chem. 1998, 63, 9904-9909.
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Mohr, B.1
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183
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0034686682
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Grubbs has prepared water-soluble catalysts that promote living ROMP and RCM reactions in aqueous and methanolic solutions (these species were not CM-active); for details of this pioneering work, see: a) B. Mohr, D. M. Lynn; R. H. Grubbs, Organometallics 1996, 15, 4317-4325; b) D. M. Lynn, B. Mohr, L. M. Henling, M. W. Day, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 6601-6609; c) D. M. Lynn, B. Mohr, R. H. Grubbs, J. Am. Chem. Soc. 1998, 120, 1627-1628; d) T. A. Kirkland, D. M. Lynn, R. H. Grubbs, J. Org. Chem. 1998, 63, 9904-9909.
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184
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0032564844
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Grubbs has prepared water-soluble catalysts that promote living ROMP and RCM reactions in aqueous and methanolic solutions (these species were not CM-active); for details of this pioneering work, see: a) B. Mohr, D. M. Lynn; R. H. Grubbs, Organometallics 1996, 15, 4317-4325; b) D. M. Lynn, B. Mohr, L. M. Henling, M. W. Day, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 6601-6609; c) D. M. Lynn, B. Mohr, R. H. Grubbs, J. Am. Chem. Soc. 1998, 120, 1627-1628; d) T. A. Kirkland, D. M. Lynn, R. H. Grubbs, J. Org. Chem. 1998, 63, 9904-9909.
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185
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0032567497
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Grubbs has prepared water-soluble catalysts that promote living ROMP and RCM reactions in aqueous and methanolic solutions (these species were not CM-active); for details of this pioneering work, see: a) B. Mohr, D. M. Lynn; R. H. Grubbs, Organometallics 1996, 15, 4317-4325; b) D. M. Lynn, B. Mohr, L. M. Henling, M. W. Day, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 6601-6609; c) D. M. Lynn, B. Mohr, R. H. Grubbs, J. Am. Chem. Soc. 1998, 120, 1627-1628; d) T. A. Kirkland, D. M. Lynn, R. H. Grubbs, J. Org. Chem. 1998, 63, 9904-9909.
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85007625716
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note
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[141] this is a further example of the utility of 4a as a metathesis tool to complement benchmark catalyst 3, which is insoluble in MeOH.
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187
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0000142128
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J. S. Kingsbury, S. B. Garber, J. M. Giftos, B. L. Gray, M. M. Okamoto, R. A. Farrer, J. T. Fourkas, A. H. Hoveyda, Angew. Chem. 2001, 113, 4381-4386; Angew. Chem. Int. Ed. 2001, 40, 4251-4256.
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For a report concerning the immobilization of a ruthenium metathesis catalyst on monolithic material by ROM-CM, see: M. Mayr, B. Mayr, M. R. Buchmeiser, Angew. Chem. 2001, 113, 3957-3960; Angew. Chem. Int. Ed. 2001, 40, 3839-3842.
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For a report concerning the immobilization of a ruthenium metathesis catalyst on monolithic material by ROM-CM, see: M. Mayr, B. Mayr, M. R. Buchmeiser, Angew. Chem. 2001, 113, 3957-3960; Angew. Chem. Int. Ed. 2001, 40, 3839-3842.
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A resin-immobilized molybdenum catalyst capable of asymmetric ROM-CM was reported recently; however, recyclability was poor: K. C. Hultzsch, J. A. Jernelius, A. H. Hoveyda, R. R. Schrock, Angew. Chem. 2002, 114, 609-613; Angew. Chem. Int. Ed. 2002, 41, 589-593.
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