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. Author manuscript; available in PMC: 2016 Jun 19.
Published in final edited form as: J Org Chem. 2015 Jun 1;80(12):6012–6024. doi: 10.1021/acs.joc.5b00794

Table 2.

Coupling of N-Phthalimidoyl Oxalate 3a with Methyl Vinyl Ketone (MVK) Under Various Reaction Conditionsa

Entry Modification Yield of 5
(%)b
1 none 82
2 reaction time of 2 h 81
3 no light <5%
4 no Hantzsch ester ND
5 no photocatalyst (2 h) 28
6 no photocatalyst (18 h) 67
7 no i-Pr2NEt•HBF4 72
8 oxalate 3a (1 equiv) 67
9 oxalate 3a (1.1 equiv) 68
10 oxalate 3a (1 equiv)
MVK (1.5 equiv)
57
a

Conditions of eq 2 using i-Pr2NEt•HBF4; [3a] = 0.15 M.

b

Isolated yield after silica gel chromatography.

ND = not detected.