Skip to main content
. 2018 Jun 5;9(26):5747–5757. doi: 10.1039/c8sc01942h

Table 2. Substrate scope of enantioselective intramolecular SN2′ reaction a .

Inline graphic
Entry 1 and 2(R) Conditions Yield b (%) ee c (%)
1 d b: 4-MeOC6H4 –60 °C, 12 h 98 79
2 d c: 4-MeC6H4 –60 °C, 12 h 96 90
3 d: 4-ClC6H4 –50 °C, 48 h 90 91
4 e: 3-MeOC6H4 –50 °C, 12 h 90 90
5 f: 3-MeC6H4 –60 °C, 48 h 97 91
6 g: 3-ClC6H4 –40 °C, 36 h 88 88
7 h: 3-CF3C6H4 –40 °C, 48 h 86 89
8 i: 2-MeOC6H4 –40 °C, 12 h 90 60
9 j: 2-MeC6H4 rt, 24 h Trace
10 k: 2-FC6H4 –20 °C, 12 h 87 87
11 d l: 2-Naphthyl –60 °C, 12 h 85 86
12 m: Ph–C Created by potrace 1.16, written by Peter Selinger 2001-2019 C– –40 °C, 48 h 55 60
13 d n: Thiophen-3-yl –60 °C, 8 h 95 91

aUnless otherwise noted, all reactions were carried out using 0.01 mmol of (R)-3d (10 mol%), 0.1 mmol of (E)-1, and MS 4A (50 mg) in chloroform (1.0 mL).

bIsolated yield.

cee was determined by chiral stationary phase HPLC analysis.

d5 mol% of (R)-3d was used.