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. Author manuscript; available in PMC: 2008 Sep 6.
Published in final edited form as: J Am Chem Soc. 2006 Oct 18;128(41):13346–13347. doi: 10.1021/ja0648108

Table 2.

Radical Additions to Pyromeconic Acid Pivalate

graphic file with name nihms-63701-t0004.jpg
Ent R1 5:6 Yld, %a drb ee, %
5 (6)c
1 i-Propyl 5c 91:9 80 99:1 70
2 c-Pentyl 5d 93:7 74 99:1 76 (36)
3 c-Hexyl 5e 92:8 55 99:1 70
4 t-Butyl 5f 90:10 76 99:1 92
5d t-Butyl 5f 93:7 60 99:1 92
6 (CH3)2C(CH2)3Cl 5g 92:8 45 99:1 95 (39)
a

Isolated yield.

b

Diastereomer ratio and site selectivity (5:6) were determined by 1H NMR (400 MHz).

c

Determined by chiral HPLC.

d

100 mol% 9.