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. Author manuscript; available in PMC: 2014 Mar 19.
Published in final edited form as: Adv Synth Catal. 2012 Nov 26;354(17):3175–3179. doi: 10.1002/adsc.201200160

Table 1.

Screening for the optimal base.a)

graphic file with name nihms-442488-t0007.jpg

entry base yieldb)[%] eec)[%]
1 KOH <5 -
2 DIPEA 61 98 (R)
3 NEt3 95 99 (R)
4d) NEt3 <5 -
5e) NEt3 92 00 (R)
6f) NEt3 58 99 (R)
a)

General procedure: 0.20 mmol cyclohexenone, 0.24 mmol PhB(OH)2, 0.006 mmol PQS-BINAP-Rh, 0.60 mmol base, and 0.4 mL H2O (0.5 M).

b)

Yield of isolated product.

c)

Determined by HPLC on chiral stationary phase.

d)

0.5 equiv base.

e)

Reaction run in 0.8 mL H2O (0.25 M).

f)

1 mol % of PQS-BINAP-Rh.