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. Author manuscript; available in PMC: 2018 Jul 5.
Published in final edited form as: J Am Chem Soc. 2017 Jun 24;139(26):9053–9065. doi: 10.1021/jacs.7b05011

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
a

Reactions were carried out under N2 atm.

b

Determined through analysis of 19F NMR spectra of the unpurified product mixtures (±2%).

c

Yields are for isolated and purified α-addition products (±5%).

d

Er was determined through HPLC analysis (±1%). See the Supporting Information for details.