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

Table 1. Temperature and concentration screening in the isocyanoacetate aldol reaction between 8 and 7a a .

Inline graphic
Entry T (°C) [7a] (M) Time (h) Yield b (%) d.r. c (trans : cis) e.e. d (%)
1 e –20 0.3 21 f 45 91 : 9 44
2 e 20 0.3 0.25 59 91 : 9 53
3 20 0.05 0.5 73 91 : 9 69
4 20 0.01 0.5 70 91 : 9 78
5 20 0.0025 17 g 70 90 : 10 80
6 0 0.01 16 f 72 90 : 10 72
7 50 0.01 2 61 88 : 12 65

aReaction performed on 0.25 mmol of 7a using 1.1 eq. of 8. Configuration of 6a 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.

e0.50 mmol of 7a.

fStirred overnight, as TLC control after 3 hours indicated that the reaction was progressing.

gStirred overnight, as TLC control after 6 hours indicated that the reaction was progressing.