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. Author manuscript; available in PMC: 2021 Feb 21.
Published in final edited form as: Org Lett. 2020 Feb 4;22(4):1681–1685. doi: 10.1021/acs.orglett.0c00342

Table 3.

Azadienolate–Alkyl Diene Coupling Scopea

graphic file with name nihms-1571772-t0005.jpg
entry product (3); R1 conv to 3 (%);b yield of 3 (%)c dr of 3b er of 3d
1e 3k; Ph(CH2)2 82; 69 4:1 88:12
2 31; n-hexyl 65; 60 4:1 81.5:18.5
3 3m; EtO2C(CH2)2 84; 83 3:1 91:9
4 3n; Cy 61; 43 3:1 90:10
5f graphic file with name nihms-1571772-t0006.jpg 83; 83 3:1 86.5:13.5
a

Reactions run under N2 with 0.15 mmol of diene 2 (0.75 M).

b

Determined by 376 MHz 19F NMR or 400 MHz 1H NMR spectroscopy of the unpurified mixture.

c

Isolated yield of purified 3.

d

Determined by HPLC analysis of purified 3.

e

A 10:1 mixture of γ-alkylation products 3k and 3k″ was formed; see ref 17.

f

11:1 3o:3o′.