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. Author manuscript; available in PMC: 2010 Nov 4.
Published in final edited form as: J Am Chem Soc. 2009 Nov 4;131(43):15909–15917. doi: 10.1021/ja906801g

Table 1.

Optimization of the Catalytic Asymmetric Diels–Alder Reactiona

graphic file with name nihms152570u1.jpg
Entry Dienophile Diene (equiv) Catalyst (mol %) Temp. (°C) Time (h) Yield (%) ee (%)
1 30 1.5 32 (5) 25 60 85 75
2 30 1.5 32 (5) −40 60 87 85
3 30 2.0 32 (5) −60 60 92 93b
4 30 1.8 40 (5) 0 2 79 76
5 31 1.8 40 (5) 0 1.5 92 93
6 31 1.5 40 (1) 0 0.5 93 94
7 31 1.1 40 (0.1) 0 0.5 97 96
8 31 1.5 none 25 0.5 5 0
a

Reactions were carried out on 0.1–1.0 mmol scale with 1.0 equiv. dienophile 30 or 31 in the presence of 4 Å M. S. in CH2Cl2.

b

Enantiomeric excess (ee) ranged from 86–93%.