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79955555357
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In the aldol reaction of trichlorosilyl enol ethers using BINAPO, more than 90% ee was observed at -78 °C, see: Ref. 4.
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For recent direct asymmetric aldol reactions, see: J. Liu, Z. Yang, Z. Wang, F. Wang, X. Chen, X. Liu, X. Feng, Z. Su, and C. Hu J. Am. Chem. Soc. 130 2008 5654
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46
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0032509531
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Trichlorosilyl triflate has been used for the preparation of trichlorosilyl enol ether by Denmark et al., see: S.E. Denmark, R.A. Stavenger, S.B.D. Winter, K.-T. Wong, and P.A. Barsanti J. Org. Chem. 63 1998 9517
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Barsanti, P.A.5
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49
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79955570943
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note
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The dichloromethane solution of trichlorosilyl triflate was storable in a refrigerator in a screw-top bottle. No loss of activity has been observed for a month.
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50
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79955559653
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note
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The yield of the aldol adduct at -78 °C was quite low and the diastereoselectivity was comparable to that at -40 °C.
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51
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79955553093
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note
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The reaction of 1b and 2a in the absence of BINAPO was completed within 5 min and the corresponding syn-isomer was produced predominantly (83% yield, syn:anti = 85:15).
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52
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79955567754
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note
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1-Boc-4-piperidone was less reactive, yielding the product in low chemical yield and stereoselectivity (24% yield, syn:anti = 28:72, 33% ee (anti)).
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