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. Author manuscript; available in PMC: 2017 Mar 8.
Published in final edited form as: Org Lett. 2016 Aug 3;18(16):3976–3979. doi: 10.1021/acs.orglett.6b01742

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
a

Isolated yields.

b

Ratios were determined by HPLC analysis using chiral stationary phase columns.

c

Reaction was performed on a 1 g scale of 1a.

d

Longer reaction times led to degradation of allenoate 2, and incomplete conversion of dienones was observed.

e

Reaction was performed on a 0.5 g scale of 1j.

f

Numbers in parentheses refer to yield based on recovered starting material.