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. 2004 Apr 5;101(16):5749–5754. doi: 10.1073/pnas.0307150101

Table 4. Enantioselective addition of alkynes to N-benzylideneaniline.

Entry Alkyne Solvent/temperature °C/time, days Yield, % OR/ee %
1 n-C3H7CCH Neat/22/4 55 (+) 71
2 Et3SiCCH Toluene/22/4 53 (+) 60
3 Cl(CH2)4CCH Toluene/22/4 48 (+) 65
4 HO(CH2)4CCH Toluene/22/4 62 (+) 85
5 HO(CH2)2CCH Toluene/22/4 58 (-) 82