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Nucleophiles with allyl-metal complexes
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Trost, B. M., Ed.; Pergamon Press: New York, Chapter 3.3
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(b) Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Chapter 3.3.
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Godleski, S.A.1
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0042997277
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note
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For method of preparation, see Supporting Information.
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17
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0001782667
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To the best of our knowledge, the Pd(0)-catalyzed intramolecular allylation using silyl enol ether with allylic carbonate has not been documented before. For an intermolecular version of this type of coupling reaction, see: (a) Tsuji, J.; Minami, I.; Shimizu, I. Chem. Lett. 1983, 1325.
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0001041487
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Tsuji, J.1
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Shimizu, I.4
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19
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0029763701
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The use of the chelating phosphine ligand dppf retarded β-hydrogen elimination (which gives acyclic diene) relative to ring closure; see (a) Hartwig, J. F.; Driver, M. S. J. Am. Chem. Soc. 1996, 118, 7217.
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Hartwig, J.F.1
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23
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33845183759
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37049086934
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Ohkata, K.1
Mase, M.2
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26
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0042496481
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note
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(b) This silyl enol ether could also be prepared from methyl tert-butyldimethylsilyl ketone and 2-propenyllithium followed by aqueous quench (84% yield) in a manner analogous to the preparation of 2 (Scheme 1).
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28
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0007929830
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(b) Vig, O. P.; Ram, B.; Atwal, K. S.; Bari, S. S. Ind. J. Chem. 1976, 14B, 855.
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85022352796
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0000861356
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(e) Takahashi, T.; Kitamura, K.; Tsuji, J. Tetrahedron Lett. 1983, 24, 4695.
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Corey, E.J.1
Daigneault, S.2
Dixon, B.R.3
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