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Volumn 125, Issue 12, 2003, Pages 3534-3543

Application of chiral mixed phosphorus/sulfur ligands to enantioselective rhodium-catalyzed dehydroamino acid hydrogenation and ketone hydrosilylation processes

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVITY;

EID: 0037467414     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja012639o     Document Type: Article
Times cited : (243)

References (79)
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    • (d) Further advances have also been made in this area with titanocene catalysts, see: Carter, M. B.; Schiott, B.; Gutierrez, A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11667-11670. Yun, J.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 5640-5644.
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    • 3; Z = 4; R = 0.0276, GooF = 1.022.
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    • For an example where the rate-determining step appears to be migratory insertion, see ref 18.
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    • 3; Z = 4; R = 0.0802, GooF = 1.219.
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    • 3; Z = 2; R = 0.0369, GooF = 1.026.
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    • There has been some confusion because the quadrant diagram has been used both to correlate the catalyst structure with the product stereochemistry and also to predict or explain the structure of the catalyst-substrate complex (often incorrectly). Here we use it for the latter purpose. (a) Knowles, W. S. Acc. Chem. Res. 1983, 16, 106-112. (b) Komarov, I. V.; Börner, A. Angew. Chem., Int. Ed. 2001, 40, 1197-1200.
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    • This has recently been claimed to be true for a bisphosphetane ligand on the basis of circumstantial evidence, but no structural data has been presented to bolster this claim. See Marinetti, A.; Jus, S.; Genet, J.-P. Tetrahedron Lett. 1999, 40, 8365-8368. Some skepticism has been expressed as to their conclusions, see footnote 21 in Landis, C. R.; Feldgus, S. Angew. Chem., Int. Ed. 2000, 39, 2863-2866
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    • For other enantioselective ketoester hydrosilylations, see: ref 39a and Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horihata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846-848. Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500-508. Kuwano, R.; Sawamura, M.; Shirai, M.; Shirai, J.; Takahashi, M.; Ito, Y. Tetrahedron Lett. 1995, 36, 5239-5242.
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    • For other enantioselective ketoester hydrosilylations, see: ref 39a and Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horihata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846-848. Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500-508. Kuwano, R.; Sawamura, M.; Shirai, M.; Shirai, J.; Takahashi, M.; Ito, Y. Tetrahedron Lett. 1995, 36, 5239-5242.
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