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. Author manuscript; available in PMC: 2010 Sep 22.
Published in final edited form as: Tetrahedron. 2009 Jan 3;65(1):17–49. doi: 10.1016/j.tet.2008.09.083

Table 7.

One-pot three-component synthesis of α-aminophosphonates (R,S)-25 and (S,S)-26.

graphic file with name nihms-111580-f0011.jpg

Entry P R R' R” Conditions Yield (%) 25 : 26 Ref.
1 H Ph i-Pr Me 2.0 M, LPDE, -15 °C 90 88 : 12 63
2 H Ph t-Bu Me 2.0M,LPDE, -15 °C 95 91 : 09 63
3 H Ph c-Hexyl Me 2.0 M, LPDE, -15 °C 94 90 : 10 63
4 Me Ph Ph Et Yb(OTf)3/MgSO4 95 78 : 22 67 a
5 Me Ph 4-MeOC6H4 Et Yb(OTf)3/MgSO4 91 78 : 22 67 a
6 Me i-Bu Ph Et Yb(OTf)3/MgSO4 82 74 : 26 67 a
7 Me i-Bu 4-MeOC6H4 Et Yb(OTf)3/MgSO4 81 74 : 26 67 a
a

The configuration of chiral auxiliary was (S) and the principal product was the diastereoisomer (S,S)-25.