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. Author manuscript; available in PMC: 2010 Jun 18.
Published in final edited form as: Org Lett. 2009 Jun 18;11(12):2715–2718. doi: 10.1021/ol900967j

Table 1.

Preparation of optically active homopropargylic allyl alcohols via CBS reduction.

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entry enone (2) allyl alcohol (3) yield (%)a ee (%)b
1 graphic file with name nihms120308t1.jpg
2a
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3a
86 87
2 graphic file with name nihms120308t3.jpg
2b
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3b
66 89
3 graphic file with name nihms120308t5.jpg
2c
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3c
95 91
4 graphic file with name nihms120308t7.jpg
2d
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3d
81 91
5 graphic file with name nihms120308t9.jpg
2e
graphic file with name nihms120308t10.jpg
3e
52 89
6 graphic file with name nihms120308t11.jpg
2f
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3f
68d 98
a

Yields of chromatographically purified products.

b

Enantiomer ratios were determined either by chiral GC or chiral HPLC.

c

Ar = 2,6-dimethoxyphenyl.

d

Reaction was quenched after 72 h.