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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 2.

Scope of the AROCM Reaction with respect to Cyclobutene Substitution.[a]

graphic file with name nihms576432u2.jpg
R1 R2 Product Yield[b] %Z[c] ee Z[d] (ee E)[d]
TBS OH 7a graphic file with name nihms576432t1.jpg 66 88 99 (nd)
H OBz 7b graphic file with name nihms576432t2.jpg 67 75 91 (67)
Bz OH 7c graphic file with name nihms576432t3.jpg 69 75 96 (82)
iPr OBz 7d graphic file with name nihms576432t4.jpg <5 nd 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.