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. Author manuscript; available in PMC: 2015 Apr 7.
Published in final edited form as: Angew Chem Int Ed Engl. 2014 Feb 19;53(15):3885–3888. doi: 10.1002/anie.201310767

Table 3.

Scope of the AROCM Reaction with respect to Terminal Olefin[a]

graphic file with name nihms576432u3.jpg
R2 Product Yield [b] % Z[c] ee Z[d] (ee E)[d]
OH 7e graphic file with name nihms576432t5.jpg 62 89 93 (86)
OBz 7f graphic file with name nihms576432t6.jpg 61 88 97 (88)
OTBS 7g graphic file with name nihms576432t7.jpg 68[e] 87 89 (77)
OBn 7h graphic file with name nihms576432t8.jpg 64 86 91 (nd)
4-MeOPh 7i graphic file with name nihms576432t9.jpg 76 90 93 (79)
CH2C(O)CH3 7j graphic file with name nihms576432t10.jpg 65 90 92 (84)
BPin 7k graphic file with name nihms576432t11.jpg 50 nd[f] 91 (nd)
[a]

0.1 mmol cyclobutene, 0.7 mmol terminal olefin.

[b]

Combined isolated yield of E and Z products.

[c]

Determined by 500 MHz 1H NMR analysis of crude reaction mixture.

[d]

Determined by chiral SFC.

[e]

Yield determined after derivatization to 7e.

[f]

Not determined due to instability of E product.