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. Author manuscript; available in PMC: 2011 Nov 5.
Published in final edited form as: J Org Chem. 2010 Nov 5;75(21):7279–7290. doi: 10.1021/jo1015008

Table 8.

Use of Cyclopentanone in Aldol Reaction.a

Entry Aldehyde Mol % (1) Conditions Yield eeb drc
1d 6 2 neat, H2O (1 equiv), 15 h, rt 87 77 (syn), 91 (anti) 1.05:1
3 6 2 neat, 24 h, rt 63 73 (syn), 74 (anti) 3.2:1
4 6 20 DCE, H2O (1 equiv), 16 h, 4°C 94 87 (syn), 95 (anti) 1.35:1
5 6 20 DCE/EtOH (99:1), 36 h, 4°C 87 85 (syn), 92 (anti) 2:1
6 16f 20 DCE, H2O (1 equiv), 48 h, 4°C 51 81 (syn), 93 (anti) 1.5:1
a

All reactions were performed at 2 M concentration of aldehyde in solution and was five equivalents of 22 unless otherwise noted.

b

Determined by chiral HPLC analysis.

c

Determined by 1H NMR analysis.

d

This reaction was performed with two equivalents of 22.