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Volumn 22, Issue 16, 2003, Pages 3205-3221

Palladium-catalyzed asymmetric phosphination. Enantioselective synthesis of PAMP-BH3, ligand effects on catalysis, and direct observation of the stereochemistry of transmetalation and reductive elimination

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; PALLADIUM; PHOSPHORUS; REDUCTION; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

EID: 0042565852     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om030144x     Document Type: Article
Times cited : (74)

References (91)
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    • (c) This statement refers to asymmetric synthesis, but biocatalytic resolution of racemic P-chirogenic phosphines, or their derivatives, yields chiral products using a catalytic amount of chiral material (enzyme). For examples, see: Shioji, K.; Tashiro, A.; Shibata, S.; Okuma, K. Tetrahedron Lett. 2003, 44, 1103-1105. Shioji, K.; Ueno, Y.; Kurauchi, Y.; Okuma, K. Tetrahedron Lett. 2001, 42, 6569. Serreqi, A. N.; Kazlauskas, R. J. J. Org. Chem. 1994, 59, 7609-7615. Kielbasinski, P.; Zurawinski, R.; Pietrusiewicz, K. M.; Zablocka, M. ; Mikolajczyk, M. Tetrahedron Lett. 1994, 35, 7081-7084.
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    • (c) This statement refers to asymmetric synthesis, but biocatalytic resolution of racemic P-chirogenic phosphines, or their derivatives, yields chiral products using a catalytic amount of chiral material (enzyme). For examples, see: Shioji, K.; Tashiro, A.; Shibata, S.; Okuma, K. Tetrahedron Lett. 2003, 44, 1103-1105. Shioji, K.; Ueno, Y.; Kurauchi, Y.; Okuma, K. Tetrahedron Lett. 2001, 42, 6569. Serreqi, A. N.; Kazlauskas, R. J. J. Org. Chem. 1994, 59, 7609-7615. Kielbasinski, P.; Zurawinski, R.; Pietrusiewicz, K. M.; Zablocka, M. ; Mikolajczyk, M. Tetrahedron Lett. 1994, 35, 7081-7084.
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    • (c) This statement refers to asymmetric synthesis, but biocatalytic resolution of racemic P-chirogenic phosphines, or their derivatives, yields chiral products using a catalytic amount of chiral material (enzyme). For examples, see: Shioji, K.; Tashiro, A.; Shibata, S.; Okuma, K. Tetrahedron Lett. 2003, 44, 1103-1105. Shioji, K.; Ueno, Y.; Kurauchi, Y.; Okuma, K. Tetrahedron Lett. 2001, 42, 6569. Serreqi, A. N.; Kazlauskas, R. J. J. Org. Chem. 1994, 59, 7609-7615. Kielbasinski, P.; Zurawinski, R.; Pietrusiewicz, K. M.; Zablocka, M. ; Mikolajczyk, M. Tetrahedron Lett. 1994, 35, 7081-7084.
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    • (c) This statement refers to asymmetric synthesis, but biocatalytic resolution of racemic P-chirogenic phosphines, or their derivatives, yields chiral products using a catalytic amount of chiral material (enzyme). For examples, see: Shioji, K.; Tashiro, A.; Shibata, S.; Okuma, K. Tetrahedron Lett. 2003, 44, 1103-1105. Shioji, K.; Ueno, Y.; Kurauchi, Y.; Okuma, K. Tetrahedron Lett. 2001, 42, 6569. Serreqi, A. N.; Kazlauskas, R. J. J. Org. Chem. 1994, 59, 7609-7615. Kielbasinski, P.; Zurawinski, R.; Pietrusiewicz, K. M.; Zablocka, M. ; Mikolajczyk, M. Tetrahedron Lett. 1994, 35, 7081-7084.
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    • During the course of this work, John Brown (Oxford) informed us that he had prepared enantioenriched chiral triarylphosphine-boranes by a similar pathway using a Pd(Tol-Binap) catalyst: Gaumont, A.-C.; Brown, J. M. Unpublished results, 1998.
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    • note
    • 11a conclusions about the stereochemistry of organometallic reaction steps are often based on indirect evidence, such as the stereochemical results of a multistep transformation, without observation, isolation, or knowledge of stereochemistry of the intermediates.
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    • 3) compounds, see: Stoop, R. M.; Mezzetti, A.; Spindler, F. Organometallics 1998, 17, 668-675. Moulin, D.; Bago, S.; Bauduin, C.; Darcel, C.; Jugé, S. Tetrahedron: Asymmetry 2000, 11, 3939-3956. Vedejs, E.; Daugulis, O.; Diver, S. T.; Powell, D. R. J. Org. Chem. 1998, 63, 2338-2341.
    • (2000) Tetrahedron: Asymmetry , vol.11 , pp. 3939-3956
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    • 3) compounds, see: Stoop, R. M.; Mezzetti, A.; Spindler, F. Organometallics 1998, 17, 668-675. Moulin, D.; Bago, S.; Bauduin, C.; Darcel, C.; Jugé, S. Tetrahedron: Asymmetry 2000, 11, 3939-3956. Vedejs, E.; Daugulis, O.; Diver, S. T.; Powell, D. R. J. Org. Chem. 1998, 63, 2338-2341.
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    • 2(PhC≡CPh) complexes, see: (a) Reference 19.
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    • note
    • Caution! We found that 2-(chloromethyl)benzothiophene caused severe contact dermatitis and suggest that special care be used in handling this compound.


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