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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 5.

Diyne scope in the asymmetric addition to aldehydesa

graphic file with name nihms190949t15.jpg

entry aldehyde R2 product % yieldb % eec
1 graphic file with name nihms190949t16.jpg graphic file with name nihms190949t17.jpg 3a 76 65
2 graphic file with name nihms190949t18.jpg graphic file with name nihms190949t19.jpg 3b 73 (49)d 82 (79) d
3d graphic file with name nihms190949t20.jpg graphic file with name nihms190949t21.jpg 7a 93 97
4e graphic file with name nihms190949t22.jpg graphic file with name nihms190949t23.jpg 7b 85 88
5e graphic file with name nihms190949t24.jpg graphic file with name nihms190949t25.jpg 7c 90 87
6 graphic file with name nihms190949t26.jpg graphic file with name nihms190949t27.jpg 7d 98 91
7 graphic file with name nihms190949t28.jpg graphic file with name nihms190949t29.jpg 7e 77 73
8 graphic file with name nihms190949t30.jpg graphic file with name nihms190949t31.jpg 7f >99 88
a

Reaction performed with 1 equiv of aldehyde and 3 equiv of diyne donor.

b

Isolated yields.

c

Enantiomeric excess determined by chiral HPLC.

d

Reaction was performed with 2 equiv of diyne and Me2Zn.

e

Catalyst loading was increased to 20 mol% 1 and 40 mol% TPPO.