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. Author manuscript; available in PMC: 2010 Mar 23.
Published in final edited form as: J Am Chem Soc. 2008 Aug 29;130(38):12592–12593. doi: 10.1021/ja805056g

Table 2.

Hydrogenative coupling of vinyl azines 1b-1d to N-toluenesulfonyl aldimines 2f, 2i and 2k.

graphic file with name nihms-90932-t0016.jpg
1b, R = Me 1c, R = Ph 1d, R = CH2OTBS
graphic file with name nihms-90932-t0017.jpg
70% Yieldb
5:1 dr, 3m 		graphic file with name nihms-90932-t0018.jpg
56% Yieldb
10:1 dr, 3n 		graphic file with name nihms-90932-t0019.jpg
77% Yield
5:1 dr, 3o
graphic file with name nihms-90932-t0020.jpg
80% Yield
4:1 dr, 3p 		graphic file with name nihms-90932-t0021.jpg
71% Yield
5:1 dr, 3q 		graphic file with name nihms-90932-t0022.jpg
67% Yield
6:1 dr, 3r
a

Cited yields are of isolated diastereomeric mixtures. Standard conditions employ 3 equiv. of 1b-1d and 1 equiv. of imines 2f, 2i and 2k. See Supporting Information for further details.

b

Reaction was performed using 7.5 mol% [Rh(cod)2]BARF and 18 mol% (2-Fur)3P.