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. 2015 Aug 27;6(12):6986–6990. doi: 10.1039/c5sc02485d

Table 1. Optimization of reaction conditions for enantioselective 3-exo-iodocyclization of allyl alcohol 1a a .

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Entry Cat. (equiv.) Additive (equiv.) T (°C) t (h) Yield b (%) ee c (%)
1 L1 (0.1) A1 (0.12) 0 40 16 30
2 L1 (0.1) A2 (0.12) 0 40 18 19
3 L1 (0.1) A3 (0.12) 0 40 44 77
4 L1 (0.1) A4 (0.12) 0 40 16 69
5 L1 (0.1) A5 (0.12) 0 40 69 86
6 L1 (0.1) A6 (0.12) 0 40 47 80
7 L1 (0.1) A7 (0.12) 0 40 65 91
8 L1 (0.1) A8 (0.12) 0 40 60 92
9 L1 (0.1) A9 (0.12) 0 40 50 91
10 0 40 ND
11 L1 (0.1) 0 40 ND
12 A8 (0.12) 0 40 ND
13 C1 (0.1) 0 40 42 83
14 C1 (0.1) A8 (0.1) 0 40 82 92
15 C1 (0.1) S Created by potrace 1.16, written by Peter Selinger 2001-2019 PPh3 (0.1) 0 40 63 90
16 d C1 (0.1) A8 (0.1) 0 40 62 69
17 e C1 (0.1) A8 (0.1) 0 40 31 67
18 C1 (0.1) A8 (0.1) –20 107 99 94

aCH2Cl2 (1 mL) was added to a mixture of silver salt L1 (0.01 mmol), ammonium salt A (0.012 mmol) and NIS (0.12 mmol), and the reaction mixture was cooled to 0 °C. Allyl alcohol 1a (0.1 mmol) in 0.5 mL CH2Cl2 was then added dropwise, and the reaction was quenched at the indicated time.

bIsolated yield.

cDetermined by HPLC using a Chiralpak AD column.

dCHCl3 as solvent.

eEtOAc as solvent. ND = not detected.