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. Author manuscript; available in PMC: 2019 Dec 1.
Published in final edited form as: Synlett. 2018 Aug 15;29(19):2481–2492. doi: 10.1055/s-0037-1610217

Table 1.

Development of conditions for the iridium-catalyzed allylic alkylation reaction of cyclic nucleophiles forming vicinal tertiary and all-carbon quaternary stereocentersa

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Entry L Additive
(X mol %)		 b:lb drb ee (%)c
1 L4 NaH (200) >95:5 1:1 99
2 L5 NaH (200) >95:5 1:2 32
3 L6 NaH (200) 95:5 >20:1 98
4 L6 - 80:20 11:1 96
5 L6 LiCl (100) 88:12 14:1 98
6 L6 LiBr (100) 95:5 >20:1 >99
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a

Reactions performed with 0.1 mmol of 25, 0.2 mmol of 24 in THF (0.1M) and allowed to proceed to complete consumption of 25.

b

Determined by 1H NMR and UHPLC-MS analysis of the crude mixture.

c

Determined by chiral HPLC analysis of the major diastereomer.

d

TBD = 1,3,5-triazabicyclo[4.4.0]dec-5-ene.