. Author manuscript; available in PMC: 2014 Apr 19.

Published in final edited form as: Org Lett. 2013 Apr 4;15(8):1994–1997. doi: 10.1021/ol4006689

Table 2.

Optimization of Enol Phosphate Reduction^a


entry	R	reducing agent	solvent	yield (%)^b (4b+5b)	4b:5b^c
1	Ph	Et₃Al	ClCH₂CH₂Cl	58	60:40
2	Ph	Et₃Al	CH₂Cl₂	62	37:63
3	Et	Et₃Al	ClCH₂CH₂Cl	70	90:10
4	Et	LiBH₄	THF	66	4b only
5	Ph	LiBH₄	THF	67	4b only

Reactions were run on 0.1 mmol scale at 0.05 M concentration with 0.2 equiv of Pd(PPh₃)₄ and 2.5 equiv of Et₃Al at 25 °C or 10 equiv of LiBH₄ at 0 °C.

¹H NMR yield.

Ratios determined by ¹H NMR spectroscopic analysis.