Table 2.
Effect of Ligand Structure on Stereoselectivity with E-Crotyl–B(pin)a
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entry | G | time (h); conv (%)b |
α:γb | Z:Eb | yield (%)c | erd |
1 | SiPh3 (ap-3) | 24; >98 | >98:2 | >98:2 | 86 | 91:9 |
2 | t-Bu (ap-4) | 24; >98 | >98:2 | 97:3 | 84 | 93:7 |
3 | H (ap-5) | 24; 71 | >98:2 | 96:4 | 60 | 89:11 |
Reactions were carried out under N2 atm.
Determined through analysis of 19F NMR spectra of the unpurified product mixtures (±2%).
Yields are for isolated and purified α-addition products (±5%).
Er was determined through HPLC analysis (±1%). See the Supporting Information for details.