Chiral aminophosphines as catalysts for enantioselective double-Michael indoline syntheses.

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
San N Khong, Ohyun Kwon

Abstract

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.

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Citations

Mar 5, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Christopher AnstissFei Liu
Sep 24, 2014·Beilstein Journal of Organic Chemistry·Yumei XiaoOhyun Kwon
Dec 16, 2020·Chemical Communications : Chem Comm·Yifan HuangHongchao Guo
Sep 12, 2018·Chemical Reviews·Huanzhen NiYixin Lu
Sep 28, 2018·Chemical Reviews·Hongchao GuoOhyun Kwon

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Methods Mentioned

BETA
acylation
column chromatography

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