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. 2017 Aug 29;8(10):7197–7202. doi: 10.1039/c7sc03183a

Table 2. Enantioselective Nazarov cyclization of 2 cooperatively catalyzed by ZnCl2 and (R)-1e: influence of N-protecting groups a .

Inline graphic
Entry R2 Product Yield b (%) er c
1 Me (2a) 3a 98 91 : 9
2 iPr (2b) 3b 98 90 : 10
3 Allyl (2c) 3c 93 89 : 11
4 Bn (2d) 3d 87 88 : 12
5 Ph (2e) 3e 90 92 : 8
6 An (2f) 3f 95 92 : 8
7 4-CF3C6H4 (2g) 3g 76 91 : 9
8 2-Np (2h) 3h 92 92 :  8

aReaction conditions: ZnCl2/(R)-1e/2 = 0.01 : 0.012 : 0.2 (mmol) in 3 mL DCE, 40 °C, 48 h.

bIsolated yield.

cDetermined by HPLC using a Chiralpak AD-3 or Chiralcel OD-3 column.