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. Author manuscript; available in PMC: 2011 Jan 27.
Published in final edited form as: Angew Chem Int Ed Engl. 2009;48(20):3648–3652. doi: 10.1002/anie.200900236

Table 1.

graphic file with name nihms176407u2.jpg
entry allylic alcohol yield (%)[a] (Z:E) dr product
1 graphic file with name nihms176407t1.jpg
2 		70 – – graphic file with name nihms176407t2.jpg
3
2 graphic file with name nihms176407t3.jpg
4 		83 – – graphic file with name nihms176407t4.jpg
5
3 graphic file with name nihms176407t5.jpg
6 		80 – – graphic file with name nihms176407t6.jpg
7
4 graphic file with name nihms176407t7.jpg
8 		87 ≥ 20:1 – graphic file with name nihms176407t8.jpg
9
5 graphic file with name nihms176407t9.jpg
10; R1 = Me; R2 = H 		81 – ≥ 20:1 graphic file with name nihms176407t10.jpg
11
6 12; R1 = H; R2 = Me 11 68 – ≥ 20:1
7 graphic file with name nihms176407t11.jpg
13 		92 1.6:1 ≥ 20:1[b] graphic file with name nihms176407t12.jpg
14
8 graphic file with name nihms176407t13.jpg
15 		57 ≤ 1:20 ≥ 20:1 graphic file with name nihms176407t14.jpg
16
9 graphic file with name nihms176407t15.jpg
17 		54 ≥ 20:1 ≥ 20:1 graphic file with name nihms176407t16.jpg
18
[a]

Reaction conditions: imine (1 eq), Ti(Oi-Pr)4 (1.5 eq), c-C5H9MgCl (3 eq) (−78 to −40 °C), then add lithium alkoxide of allylic alcohol (1.5 eq) in THF (−40 to 0 °C; or −40 °C to rt - entries 6 and 8), then quench with H2O.

[b]

Each alkene isomer (Z and E) was identified as the anti-diastereomer (dr ≥ 20:1).