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. Author manuscript; available in PMC: 2010 Jan 1.
Published in final edited form as: Angew Chem Int Ed Engl. 2009;48(13):2391–2393. doi: 10.1002/anie.200805805

Table 2.

Nucleophile-catalyzed asymmetric cycloaddition of ketenes with a nitrosoarene.

graphic file with name nihms-102360-f0009.jpg
Entry Ar R Yield (%)[a] ee (%)
1 Ph Me 72 13
2 4-(MeO)C6H4 Me 60 3
3 o-tolyl Me 90 90
4 2-(MeO)C6H4 Me 92 97
5 2-BrC6H4 Me 93 94
6 Ph Et 88 80
7 m-tolyl Et 86 78
8 1-naphthyl Et 86 78
9 o-tolyl Et 90 96
10 2-(MeO)C6H4 Et 93 (88[b]) >98 (>98[b])
11 Ph CH2CH2i-Pr 86 79
12 Ph i-Bu 90 91
13 Ph i-Pr 85 92
14 4-ClC6H4 i-Pr 84 92
15 4-(MeO)C6H4 i-Pr 81 90
16 3-thienyl i-Pr 78 84
17 Ph cyclopentyl 81 91
18 Ph cyclohexyl 84 93

All data are the average of two experiments.

[a]

Yield of purified product.

[b]

Catalyst loading: 1%.