Chiral Aminophosphines as Catalysts for Enantioselective Double-Michael Indoline Syntheses

Molecules

San N. Khong¹ 

[1] Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095, USA

关键词: double-Michael reaction;    chiral aminophosphines;    anchimeric assistance;    indoline;   

DOI  :  10.3390/molecules17055626

来源: mdpi

【 摘 要 】

The bisphosphine-catalyzed double-Michael addition of dinucleophiles to electron-deficient acetylenes is an efficient process for the synthesis of many nitrogen-containing heterocycles. Because the resulting heterocycles contain at least one stereogenic center, this double-Michael reaction would be even more useful if an asymmetric variant of the reaction were to be developed. Aminophosphines can also facilitate the double-Michael reaction and chiral amines are more readily available in Nature and synthetically; therefore, in this study we prepared several new chiral aminophosphines. When employed in the asymmetric double-Michael reaction between ortho-tosylamidophenyl malonate and 3-butyn-2-one, the chiral aminophosphines produced indolines in excellent yields with moderate asymmetric induction.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.