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. 2017 Mar 31;8(6):4347–4351. doi: 10.1039/c7sc00658f

Table 1. The catalytic asymmetric cyclopropanation of styrene with FDA a .

Inline graphic
Entry Catalyst R Solvent Temp. (°C) Yield b (%) (E) : (Z) ee c (%)
1 [Rh2(OAc)4] Et DCM 60 0
2 [Co(TPP)] Et DCM 60 <10 d
3 [Co(P1)] Et DCM 60 46 84 : 16
4 [Co(P2)] Et DCM 60 81 80 : 20 81
5 [Co(P2)] Et EtOAc 60 81 80 : 20 81
6 [Co(P2)] Et PhCl 60 73 82 : 18 83
7 [Co(P2)] Et Hexanes 60 73 80 : 20 82
8 [Co(P2)] Et Toluene 60 86 85 : 15 86
9 [Co(P2)] Et Toluene 40 73 86 : 14 90
10 [Co(P2)] Et Toluene RT 60 87 : 13 93
11 [Co(P2)] t Bu Toluene 40 78 95 : 5 96
12 e [Co( P2 )] t Bu Toluene 40 84 95:5 96
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aCarried out in one-portion under N2 with [olefin] = 0.20 M.

bIsolated yields.

cee of major (E)-diastereomer determined by chiral HPLC.

dDetermined by 1H-NMR.

eWith 5 mol% of catalyst for 20 h.