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. Author manuscript; available in PMC: 2013 Dec 30.
Published in final edited form as: Tetrahedron. 2012 Aug 7;68(52):10640–10664. doi: 10.1016/j.tet.2012.07.090

Table 1.

Asymmetric synthesis of 3-TIPSO-β-lactams 82 through chiral ester enolate-imine cyclocondensation.

Entry R1 R2 R3 β-Lactam Yield (%) ee (%)
1 Ph TMS H 82a 85 96
2 4-MeOC6H4 TMS H 82b 80 96
3 3,4-(MeO)2C6H3 TMS H 82c 80 98
4 Ph PMP PMP 82d 89 98
5 4-FC6H4 PMP PMP 82e 81 98
6 4-CF3C6H4 PMP PMP 82f 84 99
7 2-furyl PMP PMP 82g 78 92
8 (E)-PhCH=CH2 PMP PMP 82h 85 96
9 2-furyl-CH=CH2 PMP PMP 82i 72 94
10 c-C6H11CH2 PMP PMP 82j 85 90
11 Me2CHCH2 PMP PMP 82k 85 92
12 Me2C=CH PMP PMP 82l 60 94