Kotani Shunsuke, Miyazaki Shiki, Kawahara Kazuya, Shimoda Yasushi, Sugiura Masaharu, Nakajima Makoto
Graduate School of Pharmaceutical Sciences, Kumamoto University.
Chem Pharm Bull (Tokyo). 2016;64(2):189-92. doi: 10.1248/cpb.c15-00806.
2,3-Dihydro-4-pyranones were synthesized stereoselectively using a chiral phosphine oxide as the catalyst. The phosphine oxide sequentially activated silicon tetrachloride and promoted the double aldol reaction of 4-methoxy-3-buten-2-one with aldehydes. Subsequent stereoselective cyclization afforded the corresponding highly functionalized 2,3-dihydro-4-pyranones bearing three contiguous chiral centers in good yields and with high diastereo- and enantioselectivities.
使用手性氧化膦作为催化剂立体选择性地合成了2,3-二氢-4-吡喃酮。该氧化膦依次活化四氯化硅并促进4-甲氧基-3-丁烯-2-酮与醛的双羟醛反应。随后的立体选择性环化以良好的产率以及高非对映选择性和对映选择性得到了相应的带有三个相邻手性中心的高度官能化的2,3-二氢-4-吡喃酮。
