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. Author manuscript; available in PMC: 2012 Aug 17.
Published in final edited form as: J Am Chem Soc. 2011 Jul 25;133(32):12466–12469. doi: 10.1021/ja205714g

Table 1.

Base Screena

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entry base yield (%)b drc ee (%)d
1 Et3N 39 9:1 14
2e Et3N trace --- ---
3 KHMDS 25 5/1 23
4 NaOAc 62 5/1 42
5 PhCOONa 72 6/1 50
6 A1 94 5/1 57
7 A2 94 5/1 59
8 A3 76 6/1 33
9 A4 80 6/1 41
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a

Conditions: 2a, 0.2 mmol; 1a, 0.1 mmol; base, 20 mol%; C1 (structure in Table 2), 20 mol%; CH2Cl2, 1 mL; 4A MS under Ar.

b

NMR yields of trans and cis-diastereomers (internal standard).

c

The ratio of trans/cis determined by 1H NMR.

d

Ee of trans-3a determined by chiral HPLC.

e

1.2 eq of Et3N was used.