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0142161684
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note
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Application to bis-THF-ring cores has already been communicated, see ref. [7a].
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2142858450
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The absolute configurations of coupling products were determined by the modified Mosher method. See: a) I. Ohtani, T. Kusumi, Y. Kashman, H. Kakisawa, J. Am. Chem. Soc. 1991, 113, 4092-4096;
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37
-
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0142254773
-
-
note
-
1H NMR spectral data of the syn adducts appeared upfield by 0.1-0.2 ppm relative to those in the spectra of the anti adducts. On the other hand, the signals of the OH protons in the syn adducts appeared downfield by 0.1-0.2 ppm relative to those in the anti adducts. The shifts were consistent for each compound in this series.
-
-
-
-
38
-
-
0142254774
-
-
note
-
We found that a combination of the aldehyde (S)-6 with (1S&2R)-NME provided better selectivity than the corresponding combination of (S)-6 with (1R,2S)-NME. Carreira and co-workers also reported similar results in the asymmetric alkynylation of (S)-6 with acetyl propargyl alcohol,[8a] but the reaction mechanism was not mentioned.
-
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39
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0000945396
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a) O. W. Gooding, C. C. Beard, D. Y. Jackson, D. L. Wren, G. F. Cooper, J. Org. Chem. 1991, 56, 1083-1088.
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Cooper, G.F.5
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40
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0028841840
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Other synthetic procedures for 3-butyne-12-diol 13 were reported. See: b) O. Yamada, K. Ogasawara, Synthesis 1995, 1291-1294;
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0027422471
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Michel, P.1
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44
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0034700685
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During the course of our study, Pietruszka reported another solution employing the Bestmann-Ohira reagent for alkyne 13. See: J. Pietruszka, A. Witt, J. Chem. Soc. Perkin Trans. 1 2000, 4293-4300.
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Pietruszka, J.1
Witt, A.2
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45
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0142223663
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note
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Koert reported a similar double stereodifferentiation in the substrate-controlled addition of α-tetrahydrofuranic aldehyde with the chiral 3,4-isopropylidenedioxybutyl anion.[6b]
-
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46
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0031843545
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49
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0142192566
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-
note
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1H NMR spectra of related compounds. The details are described in ref. [13].
-
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51
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17244367831
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J. Yoshida, M. Nakagawa, H. Seki, Hino, J. Chem. Soc. Perkin Trans. 1 1992, 343-350.
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52
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0142254771
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1H NMR spectra of related compounds. See: a) T. B. Grindley, S. Kusuma, T. S. Cameron, Can. J. Chem. 1986, 64, 2388-2396;
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37049042197
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b) N. Baggett, K. W. Buck, A. B. Foster, M. H. Randall, J. M. Webber, J. Chem. Soc. 1965, 3394-3440.
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54
-
-
0142192565
-
-
note
-
2 was dried before use.[8d] We found that this protocol is very effective for obtaining reproducibility of the yield. Therefore, the modified procedure was employed after this entry.
-
-
-
-
55
-
-
0142161680
-
-
note
-
Carreira and co-workers reported a catalytic version of the asymmetric alkynylation.[8b] We examined the asymmetric alkynylation of the aldehyde 20 with the alkyne 25 under the catalytic conditions but the reaction did not proceed.
-
-
-
-
56
-
-
0142254772
-
-
note
-
The diastereomeric ratio based on the benzylidene acetal for 26a and 26b was almost the same as the ratio of 25a and 25b used.
-
-
-
-
59
-
-
0037017721
-
-
Recently, a one-pot THF-ring formation from the 1,2,5-triol derivatives was reported by Forsyth and co-workers. See: a) A. B. Dounay, G. J. Florence, A. Saito, C. J. Forsyth, Tetrahedron 2002, 58, 1865-1874;
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63
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0030752370
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Hoppen, S.1
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65
-
-
0142161681
-
-
note
-
The moderate yields in some entries were caused by base-promoted deprotection of the TMS group in the coupling product and subsequent coupling of the resulting acetylide with another aldehyde.
-
-
-
|