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. Author manuscript; available in PMC: 2014 May 14.
Published in final edited form as: Chem Commun (Camb). 2012 Aug 3;49(39):4376–4378. doi: 10.1039/c2cc34609e

Table 1.

Synthesis of Cyclobutene Aldehydes 6 from Alkynyl cyclopropanesa

graphic file with name nihms486840t1.jpg
Entry Substrate Productb Yield
1 graphic file with name nihms486840t2.jpg graphic file with name nihms486840t3.jpg 85%
2 graphic file with name nihms486840t4.jpg graphic file with name nihms486840t5.jpg 80%
3 graphic file with name nihms486840t6.jpg graphic file with name nihms486840t7.jpg 80%
4 graphic file with name nihms486840t8.jpg graphic file with name nihms486840t9.jpg 73%
5 graphic file with name nihms486840t10.jpg graphic file with name nihms486840t11.jpg 82%
6 graphic file with name nihms486840t12.jpg graphic file with name nihms486840t13.jpg 86%
a

Conditions: 1) CuTc (10 mol % ), AgOTf (10 mol %), 13c (1 equivalent), rt, 4-8h; 2) alumina oxide;

b

Regioselectivity (>20:1) was determined by 1H NMR of the crude product.