Diastereoselective control of intramolecular aza-Michael reactions using achiral catalysts |
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| Authors: | Zhong Cheng Wang Yikai Hung Alvin W Schreiber Stuart L Young Damian W |
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| Institution: | Chemical Biology Program, Broad Institute of Harvard and MIT, 7 Cambridge Center, Cambridge, Massachusetts 02142, USA. |
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| Abstract: | An intramolecular aza-Michael reaction with a Cbz carbamate and an enone is reported to result in 3,5-disubstituted nitrogen-containing heterocycles. Either cis or trans isomers were obtained selectively using chiral substrates and an achiral Pd(II) complex or strong Br?nsted acid catalysis. A range of substrates undergoes these selective transformations. Functionalization of the resulting products yielding bicyclic heterocycles is also demonstrated. |
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