Catalytic enantioselective construction of quaternary stereocenters by direct vinylogous Michael addition of deconjugated butenolides to nitroolefins.

نویسندگان

  • Madhu Sudan Manna
  • Vikas Kumar
  • Santanu Mukherjee
چکیده

A direct vinylogous Michael reaction of γ-substituted deconjugated butenolides with nitroolefins has been developed with the help of a newly identified quinine-derived bifunctional catalyst, allowing the synthesis of densely functionalized products with contiguous quaternary and tertiary stereocenters in excellent yield with perfect diastereoselectivity (>20:1 dr) and high enantioselectivity (up to 99:1 er).

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منابع مشابه

Synergistic Lewis base and anion-binding catalysis for the enantioselective vinylogous addition of deconjugated butenolides to allenoates.

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Catalytic Enantioselective Construction of All-Carbon Quaternary Stereocenters Catalytic Enantioselective Construction of All-Carbon Quaternary Stereocenters

SYNTHESIS 2006, No. 3, pp 0369–0396xx.xx.2006 Advanced online publication: 13.01.2006 DOI: 10.1055/s-2006-926302; Art ID: E14205SS © Georg Thieme Verlag Stuttgart · New York Abstract: Catalytic enantioselective construction of all-carbon quaternary stereocenters, i.e. carbon atoms bearing four different carbon substituents, poses a particular challenge in organic synthesis. This review gives a ...

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عنوان ژورنال:
  • Chemical communications

دوره 51 80  شماره 

صفحات  -

تاریخ انتشار 2012