Table 1. Substrate Scope for Enantioselective Synthesis of Substituted Oxatrienes.
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| entry | R | cat. | product | time (h) | yielda (%) | eeb (%) |
| 1 | Ph | A | 3a-S | 40 | 98c | 98 |
| B | 3a-R | 8 | 74 | 87 | ||
| 2 | o-OMeC6H4 | A | 3b-S | 60 | 60d | 90 |
| B | 3b-R | 60 | 65d | 82 | ||
| 3 | m-OMeC6H4 | A | 3c-S | 12 | 98 | 96 |
| B | 3c-R | 12 | 87 | 88 | ||
| 4 | p-OMeC6H4 | A | 3d-S | 60 | 25d | 94 |
| B | 3d-R | 60 | 20d | 76 | ||
| 5 | o-MeC6H4 | A | 3e-S | 40 | 75 | 88 |
| B | 3e-R | 10 | 68 | 82 | ||
| 6 | p-MeC6H4 | A | 3f-S | 60 | 43d | 94 |
| B | 3f-R | 60 | 57d | 72 | ||
| 7 | o-FC6H4 | A | 3g-S | 48 | 78 | 92 |
| B | 3g-R | 48 | 71 | 88 | ||
| 8 | o-BrC6H4 | A | 3h-S | 30 | 95 | 88 |
| B | 3h-R | 30 | 95 | 78 | ||
| 9 | p-BrC6H4 | A | 3i-S | 40 | 66 | 94 |
| B | 3i-R | 40 | 32 | 72 | ||
| 10 | o-ClC6H4 | A | 3j-S | 25 | 99e | 90 |
| B | 3j-R | 25 | 89 | 84 | ||
| 11 | p-ClC6H4 | A | 3k-S | 48 | 58 | 91 |
| B | 3k-R | 48 | 36 | 88 | ||
| 12 | 2-furyl | A | 3l-S | 48 | 27 | 95 |
| B | 3l-R | 48 | 32 | 78 | ||
| 13 | 1-naphthyl | A | 3m-S | 40 | 76 | 92 |
| B | 3m-R | 40 | 69 | 72 | ||
| 14 | n-propyl | A | 3n-S | 72 | 28 (52)d,f | 90 |
| B | 3n-R | 72 | 24 (50)d,f | 67 | ||
| 15 | isopropyl | A | 3o-S | 72 | 29 (87)d,f | 94 |
| B | 3o-R | 72 | 23 (80)d,f | 58 | ||
| 16 | Me | A | 3p-S | 36 | 48 | 90 |
| B | 3p-R | 36 | 26 | 72 | ||
Isolated yields.
Ratios were determined by HPLC analysis using chiral stationary phase columns.
Reaction was performed on a 1 g scale of 1a.
Longer reaction times led to degradation of allenoate 2, and incomplete conversion of dienones was observed.
Reaction was performed on a 0.5 g scale of 1j.
Numbers in parentheses refer to yield based on recovered starting material.