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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 *
Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095, USA
* Author to whom correspondence should be addressed.
Received: 23 March 2012 / Revised: 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 (CC BY 3.0).
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Khong, S.N.; Kwon, O. Chiral Aminophosphines as Catalysts for Enantioselective Double-Michael Indoline Syntheses. Molecules 2012, 17, 5626-5650.

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