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. Author manuscript; available in PMC: 2016 Jul 2.
Published in final edited form as: Org Lett. 2015 Jun 19;17(13):3264–3267. doi: 10.1021/acs.orglett.5b01421

Table 2.

Asymmetric Hydroformylation of Minimal-Electronically Biased 1-Alkenes.a

graphic file with name nihms728340u3.jpg
entry substrate product yield (%) b:lb erc
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1 P = TBS 18 P = TBS 19 65 2.2:1 97:3
2 P = PMB 20 P = PMB 21 60 2.3:1 95:5
3 P = Ac 22 P = Ac 23 62 2.2:1 95:5
4 P = Bz 24 P = Bz 25 69 2.6:1 96:4
5 P = THP 26 P = THP 27 37 2:1 88:12
6 P = TFA 28 P = TFA 29 63 3:1 NDd
7 graphic file with name nihms728340t15.jpg graphic file with name nihms728340t16.jpg 54 5.5:1 95:5
8 graphic file with name nihms728340t17.jpg graphic file with name nihms728340t18.jpg 66 5.2:1 NDd
9 graphic file with name nihms728340t19.jpg graphic file with name nihms728340t20.jpg 42 1.2:1 6:94e
a

Reactions performed with 0.5 mol % Rh(acac)(CO)2 and 0.55 mol % (S,S)-Ph-BPE; [substrate] = 1.0 M.

b

Branch:linear ratio determined by 1H NMR analysis.

c

See Supporting Information for details.

d

ND = not determined because of instability of related products.

e

Ligand is (R,R)-Ph-BPE for this experiment.