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E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Eds., Comprehensive Asymmetric Catalysis (Springer, Berlin, 1999), vol. 1 to 3.
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2
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84955394357
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H. Yamamoto, Ed, Wiley-VCH, New York
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H. Yamamoto, Ed., Lewis Acids in Organic Synthesis (Wiley-VCH, New York, 2000).
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(2000)
Lewis Acids in Organic Synthesis
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5
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34247564321
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I. Ojima, Ed, Wiley-VHC, New York, ed. 2, chap. 6
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I. Ojima, Ed., in Catalytic Asymmetric Synthesis (Wiley-VHC, New York, ed. 2, 2000), chap. 6.
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Catalytic Asymmetric Synthesis
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10
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32844457119
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and references therein
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B. List, Chem. Commun. 2006, 819 (2006) and references therein.
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Chem. Commun
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List, B.1
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D. R. Lide, Ed., in Handbook of Chemistry and Physics (CRC Press, New York, ed. 76, 1995), pp. 220-221.
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(1995)
Handbook of Chemistry and Physics
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13
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34247617986
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DFT calculations were performed at the B3LYP/6-311+G(2d,p)//B3LYP/6- 31G(d) level of theory using Gaussian 03 software (1-4).
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DFT calculations were performed at the B3LYP/6-311+G(2d,p)//B3LYP/6- 31G(d) level of theory using Gaussian 03 software (1-4).
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15
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K. Narasaka, T. Okauchi, K. Tanaka, M. Murakami, Chem. Lett. (Jpn.) 92, 2099 (1992).
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Narasaka, K.1
Okauchi, T.2
Tanaka, K.3
Murakami, M.4
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18
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0035861032
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H. B. Lee, M. J. Sung, S. C. Blackstock, J. K. Cha, J. Am. Chem. Soc. 123, 11322 (2001).
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Lee, H.B.1
Sung, M.J.2
Blackstock, S.C.3
Cha, J.K.4
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19
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85014927397
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P. Renaud, M. P. Sibi, Eds, Wiley-VHC, Weinheim, Germany
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P. Renaud, M. P. Sibi, Eds., Radicals in Organic Synthesis (Wiley-VHC, Weinheim, Germany, 2001), vol. 2, pp. 144-205.
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(2001)
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20
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34247587882
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Organocatalysis in combination with organometallic catalysis has previously been applied to the nonasymmetric allylation of aldehydes
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Organocatalysis in combination with organometallic catalysis has previously been applied to the nonasymmetric allylation of aldehydes.
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24
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34247589915
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Materials and methods are available as supporting online material on Science Online.
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Materials and methods are available as supporting online material on Science Online.
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25
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34247637711
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Mechanistically, we speculate that addition of the Π-rich allylsilane to the radical-cation species results in the formation of a β-silyl radical that undergoes rapid oxidation to the corresponding β-silyl cation before silyl elimination with concomitant olefin formation
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Mechanistically, we speculate that addition of the Π-rich allylsilane to the radical-cation species results in the formation of a β-silyl radical that undergoes rapid oxidation to the corresponding β-silyl cation before silyl elimination with concomitant olefin formation.
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27
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2).
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2).
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34247564066
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Bench-grade DME was found to contain sufficient water to achieve optimal results. The exclusion of water by the use of rigorously dried DME results in substantially lower chemical yields
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Bench-grade DME was found to contain sufficient water to achieve optimal results. The exclusion of water by the use of rigorously dried DME results in substantially lower chemical yields.
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The coupling of octanal with allylsilane using acetone as the bulk medium provided the corresponding allylation product in 79% ee 75% conversion after 24 hours
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The coupling of octanal with allylsilane using acetone as the bulk medium provided the corresponding allylation product in 79% ee (75% conversion after 24 hours).
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31
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M. P. Sibi, M. Hasegawa, J. Am. Chem. Soc. 129, 395 (2007); published online 16 March 2007 (10.1021/ja069245n).
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M. P. Sibi, M. Hasegawa, J. Am. Chem. Soc. 129, 395 (2007); published online 16 March 2007 (10.1021/ja069245n).
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We thank R. A. Pascal for invaluable assistance in performing Gaussian DFT calculations and M. Amatore for a late-stage experimental contribution. Financial support was provided by NIH National Institute of General Medical Sciences (grant R0l GM078201-01-01) and by gifts from Amgen, Merck Research Laboratories, and the Astellas Foundation USA. T.D.B. is grateful for a Novartis predoctoral fellowship, J.-B.H. is grateful for a KRF postdoctoral fellowship, and K.A. is grateful for a Merck overseas postdoctoral fellowship
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We thank R. A. Pascal for invaluable assistance in performing Gaussian DFT calculations and M. Amatore for a late-stage experimental contribution. Financial support was provided by NIH National Institute of General Medical Sciences (grant R0l GM078201-01-01) and by gifts from Amgen, Merck Research Laboratories, and the Astellas Foundation USA. T.D.B. is grateful for a Novartis predoctoral fellowship, J.-B.H. is grateful for a KRF postdoctoral fellowship, and K.A. is grateful for a Merck overseas postdoctoral fellowship.
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