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第 6 期                  孟春甫,等:  亚砜配体在金属催化烯丙基官能团化反应中的应用                                   ·1105·


                 nitrogen atoms as stereo controllable coordinating elements in   [30]  DU L, CAO P, XING J, et al. Hydrogen-bond-promoted palladium
                 palladium-catalyzed asymmetric allylic alkylations[J]. Tetrahedron:   catalysis: Allylic  alkylation of indoles with unsymmetrical 1,3-
                 Asymmetry, 1998, 9(21): 3797-3817.                disubstituted allyl  acetates using chiral bis(sulfoxide)  phosphine
            [12] SIEDLECKA  R,  WOJACZYŃSKA E,  SKARŻEWSKI J. Chiral   ligands[J]. Angewandte Chemie International Edition, 2013, 52(15):
                 pyrrolidine thioethers: Effective nitrogen-sulfur donating  ligands in   4207-4211.
                 palladium-catalyzed asymmetric allylic alkylations[J]. Tetrahedron:   [31]  JIA T, CAO P, WANG B,  et al. A  Cu/Pd cooperative catalysis for
                 Asymmetry, 2004, 15(9): 1437-1444.                enantioselective allylboration of alkenes[J]. Journal of the American
            [13]  NAKAMURA S,  FUKUZUMI T, TORU T. Novel chiral sulfur-   Chemical Society, 2015, 137(43): 13760-13763.
                 containing  ferrocenyl ligands for  palladium-catalyzed asymmetric   [32]  TOKUNOH R, SODEOKA M, AOE K I, et al. Synthesis and crystal
                 allylic substitution[J]. Chirality, 2004, 16(1): 10-12.   structure of a new c 2-symmetric chiral bis-sulfoxide ligand and its
            [14]  CHENG H  G, FENG B, CHEN  L  Y,  et al. Rational design  of   palladium(Ⅱ) complex[J]. Tetrahedron Letters, 1995, 36(44): 8035-
                 sulfoxide-phosphine ligands for Pd-catalyzed enantioselective allylic   8038.
                 alkylation reactions[J]. Chemical Communications, 2014, 50(22):   [33]  LIU J B, CHEN G H, XING J W, et al. Tert-butanesulfinylthioether
                 2873-2875.                                        ligands: Synthesis and application in palladium-catalyzed asymmetric
            [15]  FRAUNHOFFER  K J, PRABAGARAN N, SIROIS L E,  et al.   allylic alkylation[J]. Tetrahedron: Asymmetry, 2011, 22(5): 575-579.
                 Macrolactonization  via  hydrocarbon  oxidation[J]. Journal of the   [34]  TROST B M,  RAO M, DIESKAU A P. A chiral sulfoxide-ligated
                 American Chemical Society, 2006, 128(28): 9032-9033.   ruthenium complex for asymmetric catalysis: Enantio- and
            [16]  FRAUNHOFFER  K J, WHITE M  C. Syn-1,2-amino alcohols  via   regioselective allylic substitution[J]. Journal of the American Chemical
                 diastereoselective  allylic C—H amination[J]. Journal of the   Society, 2013, 135(49): 18697-18704.
                 American Chemical Society, 2007, 129(23): 7274-7276.   [35]  AKERMARK B, LARSSON E M, OSLOB J D. Allylic carboxylations
            [17]  BRAUN M G,  DOYLE A  G. Palladium-catalyzed allylic C—H   and lactonization  using  benzoquinone and hydrogen peroxide or
                 fluorination[J]. Journal of the American Chemical Society, 2013,   tert-butyl  hydroperoxide as oxidants[J]. The Journal of Organic
                 135(35): 12990-12993.                             Chemistry, 1994, 59(19): 5729-5733.
            [18]  LIN S, SONG C X, CAI G X, et al. Intra/intermolecular direct allylic   [36]  UMBREIT M A, SHARPLESS K B. Allylic oxidation of olefins by
                 alkylation via Pd(Ⅱ)-catalyzed allylic C—H activation[J]. Journal of   catalytic and stoichiometric selenium dioxide with  tert-butyl
                 the American Chemical Society, 2008, 130(39): 12901-12903.   hydroperoxide[J]. Journal of the American Chemical Society, 1977,
            [19]  AMMANN S E, LIU W, WHITE M C. Enantioselective allylic C—H   99(16): 5526-5528.
                 oxidation of terminal olefins to isochromans by palladium(Ⅱ)/chiral   [37]  KITCHING W, RAPPOPORT Z, WINSTEIN S, et al. Allylic
                 sulfoxide catalysis[J]. Angewandte Chemie International Edition,   oxidation  of  olefins  by palladium acetate1[J]. Journal of the
                 2016, 55(33): 9571-9575.                          American Chemical Society, 1966, 88(9): 2054-2055.
            [20]  LIU W, ALI S Z, AMMANN S E, et al. Asymmetric allylic C—H   [38]  TROST B M, METZNER P J. Reaction of olefins with palladium
                 alkylation  via  palladium(Ⅱ)/cis-ArSOX catalysis[J]. Journal of the   trifluoroacetate[J]. Journal of the American Chemical Society, 1980,
                 American Chemical Society, 2018, 140(34): 10658-10662.   102(10): 3572-3577.
            [21]  ALLEN J V, BOWER J F, WILLIAMS J M J.  Enantioselective   [39]  CHEN M S, WHITE M C. A sulfoxide-promoted, catalytic method
                 palladium catalyzed allylic substitution. Electronic and steric effects   for the regioselective synthesis of allylic acetates from monosubstituted
                 of the ligand[J]. Tetrahedron: Asymmetry, 1994, 5(10): 1895-1898.   olefins  via C—H oxidation[J]. Journal of the American Chemical
            [22]  CHELUCCI G, BERTA D, SABA A. Chiral sulfoxides and sulfides   Society, 2004, 126(5): 1346-1347.
                 tethered to pyridines as ligands for enantioselective catalysis:   [40]  ENGELIN C, JENSEN T, RODRIGUEZ-RODRIGUEZ S,  et al.
                 Palladium catalyzed allylic substitution and addition of diethylzinc to   Mechanistic investigation of  palladium-catalyzed allylic C — H
                 benzaldehyde[J]. Tetrahedron, 1997, 53(10): 3843-3848.   activation[J]. ACS Catalysis, 2013, 3(3): 294-302.
            [23]  LE FUR N, MOJOVIC L, PLÉ N,  et al. Ortho-metalation of   [41]  COVELL D J, WHITE M C.  A  chiral Lewis acid strategy for
                 enantiopure aromatic sulfoxides and  stereocontrolled addition  to   enantioselective allylic C—H oxidation[J]. Angewandte Chemie
                 imines[J]. The Journal of Organic Chemistry, 2006, 71(7): 2609-2616.   International Edition, 2008, 47(34): 6448-6451.
            [24]  HIROI K, SUZUKI  Y, KAWAGISHI R. Chiral  β-phosphino   [42]  CHEN M S, PRABAGARAN N, LABENZ N A, et al. Serial ligand
                 sulfoxides as chiral ligands in palladium-catalyzed asymmetric allylic   catalysis:  A highly selective allylic C—H oxidation[J]. Journal of the
                 nucleophilic substitution reactions[J]. Tetrahedron Letters, 1999,   American Chemical Society, 2005, 127(19): 6970-6971.
                 40(4): 715-718.                               [43]  PARENTY A, MOREAU X, CAMPAGNE J M. Macrolactonizations
            [25]  HIROI K, SUZUKI Y,  ABE I,  et al.  New chiral sulfoxide ligands   in the total synthesis of natural products[J]. Chemical Reviews, 2006,
                 possessing a phosphano or phosphanoamino functionality in   106(3): 911-939.
                 palladium-catalyzed asymmetric allylic nucleophilic substitution   [44]  STANG E M, CHRISTINA WHITE M. Total synthesis and study of
                 reactions[J]. Tetrahedron, 2000, 56(27): 4701-4710.   6-deoxyerythronolide B by late-stage C—H oxidation[J]. Nature
            [26]  CHEN J, LANG F, LI D,  et al. Palladium-catalyzed  asymmetric   Chemistry, 2009, 1(7): 547-551.
                 allylic nucleophilic substitution reactions using chiral  tert-   [45]  YOUNG A J,  WHITE M C.  Catalytic intermolecular allylic C—H
                 butanesulfinylphosphine ligands[J]. Tetrahedron: Asymmetry, 2009,   alkylation[J]. Journal of the American Chemical Society, 2008,
                 20(17): 1953-1956.                                130(43): 14090-14091.
            [27]  HIROI K, SUZUKI Y, ABE I. (S)-proline-derived new chiral ligands   [46]  HOWELL J M,  LIU W, YOUNG A J, et al. General allylic C—H
                 with phosphino, organosulfur or organoselenenyl functionality as an   alkylation with tertiary nucleophiles[J]. Journal of the American
                 enantiocontrollable coordinating element[J]. Tetrahedron: Asymmetry,   Chemical Society, 2014, 136(15): 5750-5754.
                 1999, 10(6): 1173-1188.                       [47]  YOUNG A J, WHITE M C. Allylic C—H alkylation of unactivated
            [28]  HIROI K, IZAWA  I, TAKIZAWA T,  et al.  N-phosphano nitrogen-   α-olefins: Serial ligand catalysis resumed[J]. Angewandte Chemie
                 containing five-membered aromatic chiral α-sulfoxides as new chiral   International Edition, 2011, 50(30): 6824-6827.
                 ligands in asymmetric palladium-catalyzed  allylic  alkylation:   [48]  ROGERS M M, KOTOV V, CHATWICHIEN J,  et al. Palladium-
                 Stereoelectronic effects of the substituents on the aromatic rings[J].   catalyzed oxidative  amination of  alkenes:  Improved catalyst
                 Tetrahedron, 2004, 60(9): 2155-2162.              reoxidation enables the use of alkene as the limiting  reagent[J].
            [29]  XU H, ZUEND S  J, WOLL M G,  et al. Asymmetric cooperative   Organic Letters, 2007, 9(21): 4331-4334.
                 catalysis of strong Brønsted acid-promoted reactions  using chiral
                 ureas[J]. Science, 2010, 327(5968): 986-990.                                (下转第 1269 页)
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