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. Author manuscript; available in PMC: 2012 Aug 10.
Published in final edited form as: J Am Chem Soc. 2011 Jul 18;133(31):12293–12297. doi: 10.1021/ja2049012

Table 1.

Enantioselective [3+2] Cycloadditions with a Heteroatom-Substituted Olefin: Effect of the Choice of Phosphine Catalysta

graphic file with name nihms312878u2.jpg
entry chiral catalyst ee (%)b C: D yield (%)c
1 (S,S)-DIPAMP <2 1.0: 1 59
2 (S,S)-Ph-BPE <2 1.0: 1 66
3 (S,S′, R,R′)-TangPhos 11 0.8: 1 51
4 (S)-2 −51 0.8: 1 40
5 (S)-3 59 1.1: 1 35
6 (S)-4 76 1.2: 1 88
7 (S)-1 97 1.3: 1 92
a

All data are the average of two experiments.

b

Enantiomeric excess of C. A negative value signifies that the R enantiomer was formed predominantly.

c

The yield was determined by HPLC analysis with the aid of an internal standard.