Table 3.
Azadienolate–Alkyl Diene Coupling Scopea
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entry | product (3); R1 | conv to 3 (%);b yield of 3 (%)c | dr of 3b | er of 3d |
1e | 3k; Ph(CH2)2 | 82; 69 | 4:1 | 88:12 |
2 | 31; n-hexyl | 65; 60 | 4:1 | 81.5:18.5 |
3 | 3m; EtO2C(CH2)2 | 84; 83 | 3:1 | 91:9 |
4 | 3n; Cy | 61; 43 | 3:1 | 90:10 |
5f | ![]() |
83; 83 | 3:1 | 86.5:13.5 |
Reactions run under N2 with 0.15 mmol of diene 2 (0.75 M).
Determined by 376 MHz 19F NMR or 400 MHz 1H NMR spectroscopy of the unpurified mixture.
Isolated yield of purified 3.
Determined by HPLC analysis of purified 3.
A 10:1 mixture of γ-alkylation products 3k and 3k″ was formed; see ref 17.
11:1 3o:3o′.