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. Author manuscript; available in PMC: 2013 Dec 26.
Published in final edited form as: J Am Chem Soc. 2012 Dec 12;134(51):20628–20631. doi: 10.1021/ja311208a

Table 1.

Selected optimization experiments in the ruthenium catalyzed syn-diastereo- and enantioselective hydrohydroxyalkylation of butadiene with heptanol 1a.a

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Entry Acid Ligand Ru (mol%) T(°C) Solvent (M) Yield (%) ee(%) 2a:3a
1 A1 DPPF 5 105 THF (2.0) 64 1 1:1
2 A2 DPPF 5 105 THF (2.0) 82 18 1.6:1
3 A3 DPPF 5 105 THF (2.0) 50 29 1.4:1
4 A4 DPPF 5 105 THF (2.0) 58 63 1.8:1
5 A5 DPPF 5 105 THF (2.0) 85 78 1.4:1
6 A5 (R)-Segphos 5 105 THF (2.0) 48 31 1.1:1
7 A5 (S)-Segphos 5 105 THF (2.0) 57 89 1.7:1
8 A5 (S)-Segphos 5 95 t-BuOH (2.0) 23 90 2.7:1
9 A5 (S)-Segphos 5 95 Me2CO (2.0) 46 90 3.0:1
10 A6 (S)-Segphos 5 95 Me2CO (2.0) 55 94 4.1:1
11 A6 (S)-Segphos 5 95 Me2CO (1.0) 57 94 4.6:1
⇨12 A6 (S)-Segphos 7 95 Me2CO (1.0) 82 95 4.4:1
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a

Yields are of material isolated by silica gel chromatography. DPPF = 1,1′-bis(diphenylphosphino)ferrocene; SEGPHOS = 5,5′-

bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole. See Supporting Information for further details.