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. Author manuscript; available in PMC: 2020 Sep 18.
Published in final edited form as: J Am Chem Soc. 2019 Sep 6;141(37):14904–14915. doi: 10.1021/jacs.9b08001

Table 1.

Intramolecular allylation of aldehyde 50: Key findings.

graphic file with name nihms-1055143-t0016.jpg
Entry Conditions yield of 51 yield of 53
1 CrCl2, cat. NiCl2, DMF, 60 °C 10% (2:1 dr) 17%
2 Nal, Sml2 THF/HMPA, −78 °C 27% (2:1 dr) 17%
3 Nal, Zn0, aq. NH4Cl, THF, rt – 51%
4 In0, Nal, DMF, 60 °C 13% –
5 Nal, SnCl2, DMF, 60 °Cb 90% –
a

reactions performed on a 30 mg scale, isolated yields are shown.

b

yield on 7-gram scale