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. Author manuscript; available in PMC: 2008 Dec 26.
Published in final edited form as: J Am Chem Soc. 2007 Dec 4;129(51):16119–16125. doi: 10.1021/ja0762285

Table 2.

Scope of the Catalytic Asymmetric Synthesis of (Z)-Allylic Alcohols

entry chloroalkyne Aldehyde product yielda (%) ee (%)
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1a
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2a
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3aa
61 90
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2b
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3ab
74 76
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2c
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3ac
61 95
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2d
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3ad
84 98
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2e
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3ae
69 93
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2f
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3af
72 75

7 graphic file with name nihms62834t14.jpg
1b
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2c
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3bc
63 93
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2f
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3bg
81 84

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1c
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2c
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3cc
84 88
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2e
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3ce
73 94
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2f
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3cg
74 88
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2g
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3ch
72 86
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2h
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3ci
84 93
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2i
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3cj
93 97
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2j
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3ck
73 88
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2k
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3cl
80 94

17 graphic file with name nihms62834t36.jpg
1d
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2c
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3dc
82 97
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2e
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3de
63 92
a

Yields based on aldehyde as the limiting reagent.