Asymmetric organocatalytic allylic substitution of Morita-Baylis-Hillman carbonates with allylamines for the synthesis of 2,5-dihydropyrroles |
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Authors: | Sun Wangsheng Ma Xiaozhou Hong Liang Wang Rui |
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Affiliation: | State Key Laboratory of Applied Organic Chemistry and Institute of Biochemistry and Molecular Biology, Lanzhou University, Lanzhou, 730000 China. |
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Abstract: | The asymmetric allylic substitution reaction of MBH carbonates with allylamines has been developed, which affords N-allyl-β-amino-α-methylene esters in high yields and enantioselectivities. After a subsequent ring-closure metathesis of the products, a series of optically active 2,5-dihydropyrroles could be obtained smoothly in high yields without any loss of enantioselectivity. Finally, a tentative mechanism for rationalization of the reaction has been proposed. |
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