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. Author manuscript; available in PMC: 2015 May 15.
Published in final edited form as: Angew Chem Int Ed Engl. 2014 Oct 6;53(48):13183–13187. doi: 10.1002/anie.201405854

Table 2.

α-Cyano Ketones, Amides, and Esters as Nucleophiles in Phosphepine-Catalyzed Enantioselective [4+1] Annulationsa

graphic file with name nihms687855u6.jpg
entry graphic file with name nihms687855ig1.jpg ee (%) yield (%)b
1 graphic file with name nihms687855t1.jpg R1 = H 94 85
2  OMe 94 97
3  CO2Me 94 83
4c graphic file with name nihms687855t2.jpg 90 88
5 graphic file with name nihms687855t3.jpg 93 90
6 graphic file with name nihms687855t4.jpg 93 96
7 t-Bu 94 75
8 NMe2 83 73
9 NPh2 91 93
10 graphic file with name nihms687855t5.jpg 86 73
11 graphic file with name nihms687855t6.jpg 88 86
12d OMe 82 61
a

All data are the average of two experiments.

b

Yield of purified product.

c

Reaction was run at 0 °C.

d

Reaction was run with 20% (R)–3.