Erratum: A multicomponent Ni-, Zr-, and cu-catalyzed strategy for enantioselective synthesis of alkenyl-substituted quaternary carbons, (Angewandte Chemie - International Edition (2014) 53 (1910-1914) DOI: 10.1002/anie.201309456)

Full text of DOI:10.1002/anie.201407837

Angewandte
Chemie
.
Angewandte
Corrigendum
The footnotes in Tables 1 and 2 of this communication were labeled incorrectly. The
footnote for ECA yield should be changed to [c] (previously [d]) and the footnote
corresponding to e.r. values should be changed to [d] (previously [e]). All yields are of
isolated and purified products. In Table 1, entries 7 and 8 correspond to the only reactions
for which catalyst 1c was used. In Table 2, only entries 11 and 12 relate to transformations
where catalyst precursor 1a was utilized. The accurate versions of Tables 1 and 2 are
provided below. The Supporting Information has been amended as well.
A Multicomponent Ni-, Zr-, and Cu-
Catalyzed Strategy for Enantioselective
Synthesis of Alkenyl-Substituted
Quaternary Carbons
K. P. McGrath,
A. H. Hoveyda*
1910–1914
Table 1: Multicomponent catalytic reactions with b-alkenylaluminum reagents.[a]
Angew. Chem. Int. Ed. 2014, 53
DOI: 10.1002/anie.201309456
Entry
R1; R2
ECA
conv. [%][b]
Prod.
Carbomet./acyl. yield [%];[c]
ECA yield [%][c]
e.r.[d]
1
2
3
4
5
6
7
8
9
pMeOC6H4; C6H5
pBrC6H4; C6H5
>98
>98
>98
>98
>98
>98
>98
>98
>98
3b
3c
3d
3e
3 f
3g
3h
3i
40; 75
63; 60
80; 60
80; 72
80; 60
80; 54
61; 51
80; 55
80; 60
98:2
96:4
96.5:3.5
98:2
98:2
96.5:3.5
97:3
90.5:9.5
94.5:5.5
C6H5; pMeOC6H4
C6H5; pF3CC6H4
oMeOC6H4; C6H5
C6H5; 3-thienyl
[e]
Cy; C6H5
[e]
CH2C6H5; C6H5
C6H5; Cy
3j
[a] Reactions were performed under N2 atmosphere; enones generated with >98% E selectivity in all
cases. [b] Determined by analysis of 400 MHz 1H NMR spectra of unpurified mixtures (Æ2%). [c] Yield
of isolated and purified products (Æ5%). [d] Determined by HPLC analysis; see the Supporting
Information for details. [e] NHC-Ag complex 1c was used as catalyst precursor.
Table 2: Multicomponent catalytic reactions with a-alkenylaluminum reagents.[a]
Entry
R1; R2
ECA
conv. [%][b]
Prod.
Carbomet./acyl. yield [%];[c]
ECA yield [%][c]
e.r.[d]
1
2
3
4
5
6
7
8
C6H5; C6H5
>98
>98
>98
88
>98
>98
>98
>98
>98
>98
>98
>98
>98
4a
4b
4c
4d
4e
4 f
4g
4h
4i
80; 82
40; 95
88; 88
60; 48
80; 95
80; 80
80; 97
80; 71
40; 81
63; 95
62; 87
80; 85
61; 83
99:1
97.5:2.5
99:1
99:1
98:2
97:3
98:2
99:1
98:2
99:1
95:5
97.5:2.5
92:8
pMeOC6H4; C6H5
mFC6H4; C6H5
oFC6H4; C6H5
C6H5; pMeOC6H4
C6H5; pF3CC6H4
C6H5; mF3CC6H4
C6H5; oFC6H4
pMeOC6H4; 3-thienyl
pBrC6H4; C6H5
(CH2)3OTBS; C6H5
9
10
11
12
13
4j
4k
4l
[e]
[e]
CH2C6H5; C6H5
Cy; C6H5
4m
[a] Reactions were performed under N2 atmosphere; enones generated with >98% E selectivity in all
cases. [b] Determined by analysis of 400 MHz 1H NMR spectra of unpurified mixtures (Æ2%). [c] Yield
of isolated and purified products (Æ5%). [d] Determined by HPLC analysis; see the Supporting
Information for details. [e] NHC-Ag complex 1a was used as catalyst precursor.
Angew. Chem. Int. Ed. 2014, 53, 10833 – 10847
ꢀ 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.angewandte.org 10847