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. Author manuscript; available in PMC: 2008 Sep 10.
Published in final edited form as: J Am Chem Soc. 2006 Feb 15;128(6):1840–1846. doi: 10.1021/ja055994d

Table 3.

Challenging ARCM Substrates.

graphic file with name nihms63197f9.jpg
25 to 26a 27 to 28a
catalyst ee b (%) conv c
(%)		 ee b (%) conv c
(%)
2a 16 72 −5 >98
3a 45 92 −5 >98
5a 30 93 −8 >98
2b nd <2 3 15
3b nd 6 15 18
a

Reactions with 2a-5a (2 mol %) run in CH2Cl2; catalysts 2b and 3b generated by stirring 2a and 3a (4 mol %) in THF with 25 equiv NaI.

b

Enantiomeric excesses determined by chiral GC; see supporting information for chromatograms and proof of absolute stereochemistry.

c

Determined by 1H NMR spectrum of crude reaction mixture. nd = not determined