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. Author manuscript; available in PMC: 2014 Apr 19.
Published in final edited form as: J Org Chem. 2013 Mar 29;78(8):3737–3754. doi: 10.1021/jo4002432

Table 4.

Transfer of chirality using Disubstituted Allene-ynesgraphic file with name nihms-462511-t0009.jpg

Entry Allene-ynea X R Time (h) Product, % yield % ee
1 17c NTs Me 4.6 45c, 73 81b
2 17d NTs Ph 3 45d, 84 88c
3 17f NTs TMS 3 45f, 83 84d
4 18c O Me 6.5 46c, 40 45c
5 18d O Ph 0.5 46d, 90 52c
6 18e O H 1.5 46e, 24 30e
7 18f O TMS 7 46f, 76 22d
8 19c C(CO2Et)2 Me 22 47c, 71 58f
9 19d C(CO2Et)2 Ph 1.5 47d, 96 72c
10 19f C(CO2Et)2 TMS 10 47f, 94 50d
a

The enantiomeric excess of the disubstituted allenic alcohol was >99% ee;

b

Determined using HPLC analysis (ChiralPak IA-3);

c

Determined using HPLC analysis (ChiralCel OD);

d

Determined using SFC analysis (ChiralPak IC);

e

Determined using SFC analysis (ChiralPak IA);

f

Determined using HPLC analysis (Whelk O-1).