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. Author manuscript; available in PMC: 2022 Feb 25.
Published in final edited form as: J Med Chem. 2020 Nov 17;63(23):14951–14978. doi: 10.1021/acs.jmedchem.0c01464

Table 2.

APKR with α-Methylene-γ-lactam Tether.

graphic file with name nihms-1776635-t0013.jpg
Entry Allene-yne R1 R2 APKR yield %a

1 24a Ph H 45 (72)b,c

2 25a TIPS H 46 (46)b,d

3 26 H H 47 (53)b

4 30a Ph Me 48 (75)e

5 37 Ph Ph 49 (67)b,c

6 38 Ph 4-CN-C6H4 50 (72)e

7 39 Ph 4-CF3-C6H4 51 (70)b

8 40 Ph 4-OMe-C6H4 52 (77)b

9 42 Ph 2-thiophenyl 53 (67)b

10 43 Ph Ts 54 (71)b,c

11 44 Ph boc 55 (40)b,c
a

Dropwise addition of allene-yne to rhodium catalyst over 1 h, then heated for an additional 30 min

b

Average yield for two runs

c

Similar yields were obtained when allene-yne was added in a single portion.

d

Reaction was heated for 3 h upon completion of allene-yne addition

e

Yield based upon one run.