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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 3.

Asymmetric Petasis Reaction with Boronate 6da

graphic file with name nihms54662f7.jpg
entry amine product % yieldb erc
1 graphic file with name nihms54662t1.jpg 17a 81 95:5
2 graphic file with name nihms54662t2.jpg 17b 73 93:7
3 graphic file with name nihms54662t3.jpg 17c 82 97:3
4 graphic file with name nihms54662t4.jpg 17d 80 98.5:1.5
5 graphic file with name nihms54662t5.jpg 17e 94 95:5
6 graphic file with name nihms54662t6.jpg 17f 84 95.5:4.5
7 graphic file with name nihms54662t7.jpg 17g 74 89:11
8 graphic file with name nihms54662t8.jpg 17h 87 97:3
9 graphic file with name nihms54662t9.jpg graphic file with name nihms54662t10.jpg 81 dr 90:10 (R,R:R,S)
10 graphic file with name nihms54662t11.jpg graphic file with name nihms54662t12.jpg 89 dr 84:16 (S,R:S,S)
a

Reactions were run with 0.25 mmol 6d, 0.25 mmol amine, and 15 mol % catalyst 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.