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. 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 1.

Evaluation of catalytic Lewis bases in the diynylationa

graphic file with name nihms190949t1.jpg
entry additive mol % % yieldb % eec
1 none -- 71 50
2 4Å MSd -- 59 42
3 1,2-DME 10 75 52
4 EtOAc 20 64 55
5 graphic file with name nihms190949t2.jpg 20 53 57
6 Ph3P=S 20 52 58
7 Ph3P=O 20 63 79
a

Reaction run with 3 equiv of diyne 4.

b

Isolated yield.

c

Enantiomeric excess determined by chiral HPLC.

d

Amount of molecular sieves added based on 100 mg/mmol of octanal.