Metal-Free One-Pot Synthesis of 3-Phosphinoylbenzofurans via Phospha-Michael Addition/Cyclization of H-Phosphine Oxides and in Situ Generated ortho-Quinone Methides

• DOI: 10.1021/acs.orglett.7b03863
• Publication Date: 2018-01-09T20:45:11Z
• Authors: Ji-Yuan Du; Yan-Hua Ma; Rui-Qing Yuan; Nana Xin; Shao-Zhen Nie; Chun-Lin Ma; Chen-Zhong Li; Chang-Qiu Zhao
• Keywords: 01 natural sciences; 0104 chemical sciences

A novel metal-free one-pot protocol for the effective and efficient synthesis of 3-phosphinoylbenzofurans via a phospha-Michael addition/cyclization of H-phosphine oxides and in situ generated ortho-quinone methides is described. Based on the expeditious construction of C(sp2)-P bonds, asymmetric synthesis of optically pure 3-phosphinoylbenzofurans containing chiral P-stereogenic center has also been probed by using chiral RP-(-)-menthyl phenylphosphine oxide.