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DOI: 10.1055/s-0030-1258756
Gold(I)-Catalyzed Synthesis of Furo[3,4-d]-[1,2]oxazines
F. Liu, D. Qian, L. Li, X. Zhao, J. Zhang*
East China Normal University, Shanghai and Shanghai Institute of Organic Chemistry, P. R. of China
Publikationsverlauf
Publikationsdatum:
21. Oktober 2010 (online)
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Significance
A previous regio- and diastereoselective tandem cyclization-[3+3] cycloaddition of 2-(1-allynyl)-2-alken-1-ones 1 with nitrones 2 lead to furo[3,4-d][1,2]oxazines 3 with moderate enantioselectivity using AuCl2 as catalyst and (R)-MeO-biphep as ligand (F. Liu, Y. Yu, J. Zhang Angew. Chem. Int. Ed. 2009, 48, 5505). In this report, the replacement of L3 by L1 (modification of the bite angle) or L2 (bulkier substituents on the phosphorous aryl moieties) allowed the synthesis of optically active furo[3,4-d][1,2]oxazines 3 in high yield and excellent diastereoselectivities. The choice of solvent was also crucial to keep high diastereoselectivity. The absolute configuration of products 3 was confirmed by single-crystal X-ray analysis.