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. Author manuscript; available in PMC: 2008 Aug 26.
Published in final edited form as: Chem Rev. 2007 May 27;107(6):2503–2545. doi: 10.1021/cr0509556

Table 33.

Comparison of solvent-free, highly concentrated, and standard reaction conditions for the asymmetric addition of functionalized organozinc reagents to ketones.

graphic file with name nihms-63649-t0099.jpg
entry substrates ZnR2 solvent-free or highly concentrated conditions
 standard conditions
L* (moi%) t (h) y (%) ee (%) L* (mol%) t (h) y (%) ee (%)
1 graphic file with name nihms-63649-t0100.jpg Zn((CH2)4OTBS)2 1
0.5
0.25
1		 48
70
82
40		 68
53
44
68		 79a
80a
69a
97b 		10 72 89 98
2 Zn((CH2)5Br)2 1
0.5
1		 45
50
46		 66
41
71		 92a
92a
97b 		10 72 89 96
3 graphic file with name nihms-63649-t0101.jpg Zn((CH2)5Br)2 1
0.5
0.25
0.25
1		 40
76
84
90
38		 55
47
30
30
72		 94a
94a
76a
90a,c
97b 		10 72 55 94
4 Zn((CH2)3CHMe2)2 1 18 56 94b 10 72 75 90
5 graphic file with name nihms-63649-t0102.jpg Zn((CH2)3CHMe2)2 1 27 63 93b 10 72 86 93
6 Zn((CH2)4OTBS)2 1 21 76 87b 10 120 65 90
7 Zn((CH2)5Br)2 1 36 65 89b 10 48 48 90
a

Solvent-free conditions.

b

Concentrated reaction conditions (2 equiv toluene was added to the reaction).

c

0.6 Equiv Ti(Oi-Pr)4 was used.