Institute of Organic Chemistry, RWTH Aachen University , Landoltweg 1, 52074 Aachen, Germany.
Department of Chemistry, Indian Institute of Tecnology Jammu , Jagti, NH-44, Nagrota, Jammu (J & K) 181221, India.
Org Lett. 2018 Feb 16;20(4):1232-1235. doi: 10.1021/acs.orglett.8b00175. Epub 2018 Feb 6.
An efficient and highly stereoselective one-pot, four-component synthesis of functionalized tricyclic chromanes has been achieved through an organocatalyzed quadruple domino reaction. The reaction sequence involves an oxa-Michael/Michael/Michael/aldol condensation between alcohols, 2 equiv of acrolein, and nitrochromenes to generate the pharmaceutically important tricyclic chromanes bearing three contiguous stereogenic centers including a chiral tetrasubstituted carbon center in good domino yields (30-70%) and excellent diastereo- and enantioselectivities (>20:1 dr and >99% ee).
通过有机催化的四重级联反应，实现了高效和高度对映选择性的一锅法、四组分合成功能化的三环色满。反应序列涉及醇、2 当量丙烯醛和硝基金色满之间的氧杂迈克尔/迈克尔/迈克尔/羟醛缩合，以生成具有三个连续立体中心的药物重要的三环色满，包括手性四取代碳中心，产率良好（30-70%），并且具有极好的非对映选择性和对映选择性（>20:1 dr 和 >99%ee）。
