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. Author manuscript; available in PMC: 2019 Jul 6.
Published in final edited form as: Org Lett. 2018 Jun 25;20(13):4144–4147. doi: 10.1021/acs.orglett.8b01776

Table 1.

Enantioselective iridium-catalyzed allylation of ynals 1a-1f with allyl acetate via 2-propanol-mediated reductive coupling.a

graphic file with name nihms-993307-t0005.jpg
entry 1a-1d catalyst yield (%) ee (%)
1 1a, R = Ph (S)-lr-l — —
2 1a, R = Ph (S)-lr-ll — —
3 1b, R = CH2OTBDPS (S)-lr-l — —
4 1b, R = CH2OTBDPS (S)-lr-ll — —
5 1c, R = CMe2OTIPS (S)-lr-l 63 95
6 1c, R = CMe2OTIPS (S)-lr-ll 53 94
7 1d, R = TMS (S)-lr-l — —
8 1d, R = TMS (S)-lr-ll — —
9 1e, R = TBS (S)-lr-l 24 94
10 1e, R = TBS (S)-lr-ll 22 96
11 1f, R = TIPS (S)-lr-l 78 95
12 1f, R = TIPS (S)-lr-ll 61 93
graphic file with name nihms-993307-t0006.jpg
a

Yields are of material isolated by silica gel chromatography. Enantioselectivity was determined by chiral stationary phase HPLC analysis. See Supporting Information for further experimental details.