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. Author manuscript; available in PMC: 2012 Dec 7.
Published in final edited form as: J Am Chem Soc. 2011 Nov 10;133(48):19483–19497. doi: 10.1021/ja207550t

Table 4.

Deprotection of N-Boc Pyrrolidines and Phosphoramidite Synthesis.

entry N-Boc pyrrolidine R1 R2 pyrrolidine yield (%) ligand yield (%)
1 10a C6H5 H 12a 92 L34 38
2 11ab C6H5 2-OMeC6H4 12ab 97 L35 81
3 11ac C6H5 2-Naphthyl 12ac 100 L36 82
4 11ba 2-MeOC6H4 2-MeOC6H4 12ba 71 L37 41
5 11ca 2-Naphthyl 2-Naphthyl 12ca 98 L38 84
6 11cb 2-Naphthyl 1-Naphthyl 12cb 100 L39 77
7 11cc 2-Naphthyl 3,5-t-BuC6H3 12cc 86 L40 68
8 11d 3-Biphenyl 3-Biphenyl 12d 97 L41 40
9 11e 3,5-PhC6H3 3,5-PhC6H3 12e 92 L42 68
10 11f 4-Biphenyl 4-Biphenyl 12f 99 L43 82
11 11g 1-Naphthyl 1-Naphthyl 12g 10a L44 60
a

Isolated yield for two steps from 10g