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. Author manuscript; available in PMC: 2009 Feb 2.
Published in final edited form as: J Org Chem. 2006 Mar 31;71(7):2630–2640. doi: 10.1021/jo052383v

Table.

Stereoselectivities of reactions of arylcuprates with trans and cis α,β-enoates with a single γ-alkoxy stereocenter

graphic file with name nihms-63101-t0015.jpg

enoate adduct % yield anti:syn

trans enoates

1 12a 80 > 50:1
1 12b 78 > 50:1
1 12c 79 > 50:1
1 12d 75 > 50:1
1 12e 76 > 50:1
1 12f 75 > 50:1
2 13a 88 > 50:1
2 13d 93 > 50:1
2 13f 82 > 50:1
3 14a 94 14.6:1
3 14d 76 11.3:1
3 14f 88 9.9:1
4 15a 89 5.4:1
4 15d 80 6.1:1
4 15f 82 5.9:1

cis enoates

5 16a 87 1.6:1
5 16d 69 1:1.3
5 16f 53 1:1.3
6 17a 72 2.8:1
6 17d 68 2.7:1
6 17f 63 2.9:1
7 18a 65 3.4:1
7 18d 56 1.9:1
7 18f 54 2.2:1