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. Author manuscript; available in PMC: 2012 Apr 13.
Published in final edited form as: J Am Chem Soc. 2011 Mar 23;133(14):5500–5507. doi: 10.1021/ja200084a

Table 4.

Substrate Scope for AuI-catalyzed Cycloaddition/Alkoxylation of Allenenes with 11c.a

entry Substrate NuH 3 yield % ee %
graphic file with name nihms-283576-t0010.jpg graphic file with name nihms-283576-t0011.jpg
R1, R2
1 2-OMe-C6H4, H MeOH d 73 96
2 3-OMe-C6H4, H MeOH e 92 96
3 4-OMe-C6H4, H MeOH f 90 94
4 4-Cl-C6H4, H MeOH g 68 86
5 Ph, H EtOH h 90 92
6 Ph, H HOCH2(C(CH3)3) i 72 94
7 Ph, H HOCH2(HC=CH2) j 84 94
8 Ph, H HOCH(CH3)2 k 81 96
9 Ph, H H2O l 85 96
10 Ph, H MeOH b 95 94
11 H, Ph MeOH b 39 86
12 Ph, Me MeOH m 83 92
graphic file with name nihms-283576-t0012.jpg graphic file with name nihms-283576-t0013.jpg
13 MeOH n 76 94
graphic file with name nihms-283576-t0014.jpg graphic file with name nihms-283576-t0015.jpg
14 MeOH o 86 72
a

Reaction conditions: 11c (6 mol%), AgBF4 (5 mol%), trapping agent (Nu) (9 equiv), 24h. For entries 5-10 the reaction was run at 0°C, all others were run at room temperature. In all experiments a small amount (<9%) of the corresponding [2+2]-cycloaddition product was also produced. The diastereoselectivity was >98:2 in all cases. Isolated yields after silica gel flash column chromatography. Enantiomeric excess determined by enantiodiscriminating HPLC (see Supporting Information).