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. Author manuscript; available in PMC: 2010 Jan 21.
Published in final edited form as: J Am Chem Soc. 2009 Jan 21;131(2):570–576. doi: 10.1021/ja8062315

Table 3.

Dependence of Ag-catalyzed AVM selectivity on temperaturea

graphic file with name nihms-86754-t0010.jpg
entry temp (°C) 7a:8ab yield (%)c 7a er; ee (%)d 8a er; ee (%)d
1 −78 93:7 88 95.5:4.5; 91 82.5:17.5; 65
2 −50 33:66 76 85:15; 70 85:15; 70
3 −30 14:86 58 58:42; 16 81:19; 62
4 −15 10:90 32 63:37; 26 79.5:20.5; 59
5 +4 8:92 41 <55:45; <10 77:23; 54
a

Reactions performed under N2 atmosphere; all reactions were quenched at the specified temperature and kept at that temperature for 3 hours before allowing to warm to 22 °C. All conversions = >98% (substrate consumption based on internal standard).

b

Diastereomeric ratios were determined by 400 MHz 1H NMR analyses of product mixtures prior to purification.

c

Yields are of purified products; with the exception of entry 1 (yield of only anti-7a), total yields of isomeric mixtures are shown.

d

Enantiomer ratio (er) values were determined by chiral HPLC analysis; see the Supporting Information for details.