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Molecules 2012, 17(5), 5626-5650; doi:10.3390/molecules17055626
Article

Chiral Aminophosphines as Catalysts for Enantioselective Double-Michael Indoline Syntheses

 and *
Received: 23 March 2012; in revised form: 19 April 2012 / Accepted: 23 April 2012 / Published: 11 May 2012
(This article belongs to the Special Issue Asymmetric Catalysis)
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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.
Keywords: double-Michael reaction; chiral aminophosphines; anchimeric assistance; indoline double-Michael reaction; chiral aminophosphines; anchimeric assistance; indoline
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Khong, S.N.; Kwon, O. Chiral Aminophosphines as Catalysts for Enantioselective Double-Michael Indoline Syntheses. Molecules 2012, 17, 5626-5650.

AMA Style

Khong SN, Kwon O. Chiral Aminophosphines as Catalysts for Enantioselective Double-Michael Indoline Syntheses. Molecules. 2012; 17(5):5626-5650.

Chicago/Turabian Style

Khong, San N.; Kwon, Ohyun. 2012. "Chiral Aminophosphines as Catalysts for Enantioselective Double-Michael Indoline Syntheses." Molecules 17, no. 5: 5626-5650.



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