FULL PAPERS
Enantioselective a-Alkylation of Benzylideneamino tert-Butyl Malonates
CDCl3): d=8.23 (s, 1H), 7.59 (q, J=7.75 Hz, 4H), 7.25–7.15
(m, 5H), 3.26 (q, J=12.63 Hz, 2H), 1.44 (s, 9H), 1.38 (s,
3H); 13C NMR (600 MHz, CDCl3): d=170.2, 169.2, 155.2,
135.9, 132.2, 130.3, 129.8, 128.8, 128.2, 126.9, 126.4, 82.1,
54.8, 41.0, 27.8, 19.9; IR (KBr): n=3839, 2980, 1776, 1734,
1590, 1488, 1455, 1369, 1253, 1151, 1113, 1083, 1011, 925,
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847, 821, 735, 701 cmÀ1
; HR-MS(FAB): m/z=446.0952,
calcd. for [C22H24BrNO4]+: 445.0889. The enantioselectivity
was determined by chiral HPLC analysis (DAICEL Chiral-
pak AS-H, hexane:2-propanol=90:10, flow rate=
1.0 mLminÀ1, 238C, l=256 nm): retention times S isomer
(minor) 11.1 min, R isomer (major) 12.1 min; 97% ee; [a]2D5:
+60.70 (c 1.0, CHCl3).
Acknowledgements
This work was supported by the National Research Founda-
tion of Korea Grant funded by the Korean Government (No.
2007-0056817, 2009-0083533). This work was also supported
by BK21 Plus Program in 2015.
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