. Author manuscript; available in PMC: 2011 Apr 14.

Published in final edited form as: J Am Chem Soc. 2010 Apr 14;132(14):5186–5192. doi: 10.1021/ja910656b

Table 3.

Optimization of TPPO stoichiometry^a

entry	mol% TPPO	% yield^b	% ee^c
1	10	65	73
2	20	63	79
3	50	66	77
4	100	57	77

Reaction as shown in eq 4 with 1 equiv of octanal, 3 equiv of diyne 4, 10 mol% 1 and 3 equiv of Me₂Zn.

Isolated yield of diynol 5.

Enantiomeric excess of 5 determined by chiral HPLC.