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. 2015 Oct 29;14(1):93–96. doi: 10.1039/c5ob02141c

Table 2. Pronucleophile and ligand screening in the isocyanoacetate aldol reaction between 8 and 7 a .

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Entry R 7 Ligand Time (min) Yield b (%) d.r. c (trans : cis) e.e. d (%)
1 (CH3)3C 7a L-1 30 70 91 : 9 78
2 CH3 7b L-1 100 80 88 : 12 82
3 PhCH2 7c L-1 180 61 90 : 10 87
4 PhCH2 7c L-2 80 64 90 : 10 87
5 4-(OCH3) C6H4CH2 7d L-2 60 63 89 : 11 86
6 3,5-(CF3)2 C6H3CH2 7e L-2 60 56 90 : 10 84
7 Ph2CH 7f L-1 100 81 93 : 7 87
8 Ph2CH 7f L-2 45 78 91 : 9 89
9 Ph2CH 7f L-3 200 82 93 : 7 88 e
10 Ph2CH 7f L-4 60 68 92 : 8 93 e

aReaction performed on 0.25 mmol of 7 (0.01 M in AcOEt) using 1.1 eq. of 8. Configuration of 6 assigned by analogy with previous work.9

bIsolated yield of trans diastereomer after FCC.

cd.r. determined by 1H NMR analysis of the crude reaction mixture.

de.e. of trans diastereomer determined by HPLC on chiral stationary phase.

eOpposite enantiomer obtained.