title: Asymmetric organocatalytic allylic substitution of Morita-Baylis-Hillman carbonates with allylamines for the synthesis of 2,5-dihydropyrroles.
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.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry and Institute of Biochemistry and Molecular Biology, Lanzhou University, Lanzhou, 730000 China.
authors.forename: Wangsheng
authors.initials: W
authors.lastname: Sun
authors.forename: Xiaozhou
authors.initials: X
authors.lastname: Ma
authors.forename: Liang
authors.initials: L
authors.lastname: Hong
authors.forename: Rui
authors.initials: R
authors.lastname: Wang
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000499:Allylamine / Q000737:chemistry*; D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000475:Alkenes; D002254:Carbonates; D011758:Pyrroles; D000499:Allylamine