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a values in water of tetrazoles lie in the range of -0.8 to about 6 depending on the electronic properties of the substituent at position 5 of the tetrazole ring, see: A. A. A. Boraei, J. Chem. Eng. Data 2001, 46, 939.
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4544311420
-
-
note
-
In some respects, our results compare well with the proline-catalyzed reactions.[3] However, what is different from proline is enhanced reactivity leading to a lower catalyst (5-10 mol %) and ketone (1-8 equiv) loading, and even more expanded substrate scope regarding the ketone component. See also the Supporting Information for comparison experiments with proline.
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-
-
-
54
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0141519517
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After we finished this work, the following important papers were published, which also support our mechanism, see: a) K. Funabiki, N. Honma, W. Hashimoto, M. Matsui, Org. Lett. 2003, 5, 2059;
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Matsui, M.7
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56
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4544291009
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note
-
3CN or MeOD at room temperature for one day.
-
-
-
-
57
-
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4544325433
-
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note
-
The absolute configuration of 4 and 5 was determined by X-ray single-crystal analysis. See the Supporting Information.
-
-
-
-
58
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0000584420
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(Ed.: J. D. Morrison), Academic Press, San Diego
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Heathcock, C.H.1
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Ab initio calculation of proline- or amine-catalyzed aldol reactions, see: b) K. N. Rankin, J. W. Gauld, R. J. Boyd, J. Phys. Chem. A 2002, 106, 5155;
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Rankin, K.N.1
Gauld, J.W.2
Boyd, R.J.3
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62
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4544388438
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note
-
This enantioselective hydroxymethylation is now under investigation with other carbonyl compounds, and the results will appear in a full account.
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