Table 1.
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entry | enyne | cp yielda | conditions Ab | yieldc | conditions Bb | yieldc |
1 | 7 94% | 8 81% | 9 79% | |||
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2 | 11 83% | 12 72% | 13 66% | |||
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3 | 15 82% | 16 31% (+ 54% 17) | 17 80% (15:1)d | |||
4 | 19 72% | 20 93% | 21 25% (1:1)d (+ 62% 20) | |||
5 | 23 75% | 24 60% | 25 85% (1.6:1)d | |||
| ||||||
6 | 27 41% | 28 58% | 29 76% | |||
7 | 31 62% | 32 86% | 33 93% | |||
8 | 35 79% | 36 83% | 37 63% | |||
9 | 39 79% | 40 95% | 41 59% | |||
10 | 43 87% | 44 71% | 45 60% | |||
11 | 47 73% | 48 89% | 49 71% | |||
12 | 51 74% | 52 64% | 53 90% | |||
| ||||||
13 | 55 77% | 56 69% | 57 79% | |||
| ||||||
14 | 59 50% | 60 65% | N/Ae | |||
15 | 62 62% | 63 53% | ||||
16 | 65 58% | 66 66% |
Isolated yields of cis-cyclopropane Reactions run with 3:1 ratio of 1:enyne.
A: 5% AgOTf, 5% (ArO)3PAuCl, CH2Cl2. B: 5% AgSbF6, 5% (ArO)3PAuCl, CH2Cl2.
Isolated yields
Ratio of regioisomers.
Conditions B were not investigated with 58, 61 and 64.