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. 2019 Dec 10;15:2948–2957. doi: 10.3762/bjoc.15.290

Table 1.

Ireland–Claisen rearrangement of 1ac with LDA as the base without organocatalysts.

Entry R R’3SiX (equiv) Temperature (°C) Time (h) Yield of 2 (%) dr

1 H Me3SiCl (1.1) rt 168 63
2 H Me3SiCl (1.1) 66 3 41
3 Me Me3SiCl (1.1) rt 72 42 76:24
4 Me Me3SiCl (1.1) 66 2 36 76:24
5 Me Me3SiCl (1.1) rt 20 38 77:23
6 Me rt 20 30 79:21
7 Ph Me3SiCl (1.0) rt 168 0
8 Ph t-BuMe2SiOTf (1.1) rt 168 0