Enantioselective synthesis of nitrocyclopropanes via conjugate addition of bromomalonate to nitroalkenes catalyzed by Ni(II) complexes

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초록

A novel one-pot methodology for the catalytic enantioselective synthesis of highly functionalized nitrocyclopropanes promoted by chiral nickel complexes is developed. The treatment of bromomalonates with nitroalkenes under the mild reaction conditions afforded the corresponding Michael adducts which cyclizes to controlled reaction conditions with excellent diasteroselectivities (>99 de) and enantioselectivities (up to 99% ee). (C) 2012 Elsevier Ltd. All rights reserved.

키워드

CyclopropanationAsymmetric catalysisChiral nickel catalystsNitroalkenesConjugate additionELECTROPHILIC ALPHA-AMINATIONMANNICH-TYPE REACTIONSBETA-KETO-ESTERSSTEREOSELECTIVE-SYNTHESIS1,3-DICARBONYL COMPOUNDSALKYLATION REACTIONSMICHAEL ADDITIONSFLUORINATIONCYCLOPROPANATIONCYANOKETONES
제목
Enantioselective synthesis of nitrocyclopropanes via conjugate addition of bromomalonate to nitroalkenes catalyzed by Ni(II) complexes
저자
Lee, Hyun JooKim, Sun MiKim, Dae Young
DOI
10.1016/j.tetlet.2012.04.072
발행일
2012-07-04
유형
Article
저널명
Tetrahedron Letters
53
27
페이지
3437 ~ 3439