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. Author manuscript; available in PMC: 2009 Jun 4.
Published in final edited form as: J Am Chem Soc. 2008 May 7;130(22):6922–6923. doi: 10.1021/ja8018934

Table 2.

Asymmetric Petasis Reaction with Dibenzylamine 7a

graphic file with name nihms54662f6.jpg
entry R1 R2 product % yieldb erc
1 Ph H 15a 81 95.5:4.5
2 p-CH3O-C6H4 H 15b 84 96:4
3 p-Br-C6H4 H 15c 82 95:5
4 m-F-C6H4 H 15d 80 95:5
5 m-CF3-C6H4 H 15e 82 95:5
6 3-C4H3S H 15f 87 95:5
7d C6H11 H 15g 76 97:3
8d n-Bu H 15h 73 95:5
9d BnOCH2 H 15i 74 95.5:4.5
10 Ph CH3 15j 78 95:5
11d n-Bu CH3 15k 71 93:7
a

Reactions were run with 0.25 mmol 14, 0.25 mmol amine, 0.25 mmol glyoxylate, 0.0375 mmol (S)-5j, and 3Å molecular sieves in toluene for 36 h under Ar, followed by flash chromatography on silica gel.

b

Isolated yield.

c

Determined by chiral HPLC analysis.

d

Reactions were run at 0 °C.