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(2) For leading references on catalytic asymmetric aldol additions see: (a) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463.
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(3) For examples of primarily anti-selective catalytic asymmetric aldol additions, see: (a) Evans, D. A.; MacMillan, D. W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859.
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(5) Recently Yamamoto has described a silver(I)-catalyzed aldol addition of stannyl enolates to aldehydes which also correlates starting enolate geometry and the major diastereomer: Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319.
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0010483857
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(7) (a) Burlachenko, G. S.; Khasapov, B. N.; Petrovskaya, L. I.; Baukov, Yu. I.; Lutsenko, I. F.; J. Gen. Chem. USSR (Engl. Transl.) 1966, 36, 532.
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(b) Ponomarev, S. V.; Baukov, Yu. I.; Dudukina, O. V.; Petrosyan, I. V.; Petrovskaya, L. I. J. Gen. Chem. USSR (Engl. Transl.) 1967, 37, 2092.
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(8) For a review of the conversion of TMS enol ethers to reactive enolates see: Kuwajima, I.; Nakamura, E. Acc. Chem. Res. 1985, 18, 181.
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(9) House, H. O.; Auerbach, R. A.; Gall, M.; Peet, N. P. J. Org. Chem. 1973, 38, 514.
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21
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0010442589
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note
-
(10) The relative configuration was established on the basis of the splitting pattern and resonance frequency of the hydroxyl bearing methine. The proton appears as a broad singlet in the syn-isomer and as a doublet or doublet of doublets in the anti-isomer. In addition, this proton in the anti-isomer appears 0.4-0.7 ppm upfield of the syn-isomer.
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-
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22
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0000019167
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(11) (a) Denmark, S. E.; Griedel, B. D.; Coe, D. M.; Schnute, M. E. J. Am. Chem. Soc. 1994, 116, 7026.
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Schnute, M.E.4
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23
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0010518375
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See also ref. 4b
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(b) See also ref. 4b.
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25
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0000250254
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(b) Myers, A. G.; Widdowson, K. L.; Kukkola, P. J. J. Am. Chem. Soc. 1992, 114, 2765.
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(13) Gung, B. W.; Zhu, Z.; Fouch, R. A. J. Org. Chem. 1995, 60, 2860.
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(15) Enol borates: (a) Hoffmann, R. W.; Ditrich, K.; Froech, S.; Cremer, D. Tetrahedron 1985, 41, 5517.
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0000928577
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Enol boronates see
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(b) Gennari, C.; Todeschini, R.; Beretta, M. G.; Favini, G.; Scolastico, C.; J. Org. Chem. 1986, 51, 612. Enol boronates see:
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0001924338
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Allinger, N. L.; Eliel, E. L.; Wilen, S. H., Eds.; Wiley Interscience: New York, See also refs. 8 and 16
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(b) Evans, D. A.; Nelson, J. V.; Taber, T. R. in Topics in Stereochemistry; Allinger, N. L.; Eliel, E. L.; Wilen, S. H., Eds.; Wiley Interscience: New York, 1982; Vol. 13, p1. See also refs. 8 and 16.
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Nelson, J.V.2
Taber, T.R.3
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33
-
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0010445805
-
-
note
-
(17) The absolute configuration of the (-)-anti-5c was determined to be (2R,1′S) by X-ray crystallographic analysis of the corresponding 4-bromobenzoate. The absolute configurations of the other anti diastereomers are assigned by analogy. The absolute configurations of the syn diastereomers were not established.
-
-
-
-
34
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0001214450
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(18) For a review on the reactivity of hypervalent silicon species see: Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371.
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Chuit, C.1
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(19) Bockman, T. M.; Shukla, D.; Kochi, J. K. J. Chem. Soc., Perkin Trans. 2 1996, 1623.
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Bockman, T.M.1
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Kochi, J.K.3
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