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. 2014 Dec 10;80(1):313–366. doi: 10.1021/jo502388r

Table 7. SAR and SSR Studies of Hydrazone Ligands for the Coupling of 2-Methylnaphthylsilanolate (K+35a).

3.2.

entry ligand time (h) 37a (%) 38b (%) er, 37 (R/S)c
1 13a 2 81 2.0 6:94
2 13f 2 86 1.4 5:95
3 21a 4 70 3.5 40:60
4 21f 6 76 2.8 43:57
5 29 4 78 6.6 48:52
6 15 2d ∼21e 12.8 50:50
7 33a 2 84 3.0 19:81
8 33b 18 59f 9.0 68:32
9 34 24 34 8.8 52:48
a

Yield of chromatographed product taking into account of 1,1′-binaphthalene.

b

Percentage of 1,1′-binaphthalene in the chromatographed product estimated by CSP-SFC.

c

Ratio of (R)-37:(S)-37 determined by CSP-SFC.

d

Reaction stalled.

e

Contains a contaminant.

f

0.1 mmol scale.f