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. 2015 Dec 16;55(5):1797–1800. doi: 10.1002/anie.201510602

Table 1.

Substrate scope for the nitroalkene bearing an internal alkynes with a phenyl substituent.[a]Inline graphic

4 R1 R2 Yield [%][b] d.r.[c] ee [%][d]
a Me Ph 99 10:1 90
b Et Ph 83 >20:1 93
c iPr Ph 74 >20:1 92
d Ph Ph 95 6:1 91
e Me 2-Cl-C6H4 73 10:1 82
f Me 4-Me-C6H4 89 10:1 99
g[e] Me Me 59 20:3 86

[a] Reaction conditions: 1 (0.33 mmol), 2 (0.3 mmol), DHQN-SA1 (3 mol %), CHCl3 (1.2 mL), RT, 1–2 h. [b] Yield of 4 after flash chromatography. [c] Determined by 1H NMR spectroscopy. [d] Determined by HPLC using a chiral stationary phase. [e] The formation of small amounts of an additional diastereomer or regioisomer was detected.