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. Author manuscript; available in PMC: 2018 Jul 23.
Published in final edited form as: J Org Chem. 2009 Jun 19;74(12):4508–4518. doi: 10.1021/jo900642f

Table 1. The Alkylation of Lactone 1 with Various Electrophiles.

graphic file with name nihms-977331-t0010.jpg
entry R X product % yield dra
1 −CH3 I 5a 75 16:1
2 −CH2CH3 I 5b 67 17:1
3 −CH2CN Br 5c 76 17:1
4 −CH2C6H5 Br 5d 63 99:1
5 −CH2-C6H5-pNO2 Br 5e 71 99:1
6 −CH2CH2CHCH2 Br 5f 32 20:1
a

The dr was determined by 1H NMR of the crude reaction mixture.