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. Author manuscript; available in PMC: 2011 Mar 5.
Published in final edited form as: J Org Chem. 2010 Mar 5;75(5):1795–1798. doi: 10.1021/jo902697g

Table 1.

Enantioselective Carbonyl Allylation of Furan Methanols via Iridium Catalyzed Transfer Hydrogenation.a

graphic file with name nihms177153u2.jpg
Entry Furan Methanol Product Isolated Yield ee (%)
1 R = H, 1a 3a 69% 92 (R)
2 R = Me, 1b 3b 75% 95 (R)
3 R=Ar, 1c 3c 79% 94 (R)
a

Yields are of material isolated by silica gel chromatography. Enantiomeric excess was determined by chiral stationary phase HPLC analysis. For compound 1c, Ar = 3-chloro-4-methoxyphenyl. See Supporting Information for additional details.