Enantioselective direct vinylogous michael addition of functionalized furanones to nitroalkenes catalyzed by an axially chiral guanidine base

Masahiro Terada; Kenichi Ando

doi:10.1021/ol200415u

Enantioselective direct vinylogous michael addition of functionalized furanones to nitroalkenes catalyzed by an axially chiral guanidine base

Masahiro Terada, Kenichi Ando

SCI - Chemistry

Research output: Contribution to journal › Article › peer-review

63 Citations (Scopus)

Abstract

The highly syn-diastereo- and enantioselective direct vinylogous Michael addition ofα-thio substituted furanones with conjugate nitroalkenes was demonstrated using an axially chiral guanidine base catalyst. The method provides facile access to enantioenriched α,γ-functionalized butenolides that can be further manipulated, thereby rendering them useful synthetic intermediates.

Original language	English
Pages (from-to)	2026-2029
Number of pages	4
Journal	Organic letters
Volume	13
Issue number	8
DOIs	https://doi.org/10.1021/ol200415u
Publication status	Published - 2011 Apr 15

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol200415u

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abstract = "The highly syn-diastereo- and enantioselective direct vinylogous Michael addition ofα-thio substituted furanones with conjugate nitroalkenes was demonstrated using an axially chiral guanidine base catalyst. The method provides facile access to enantioenriched α,γ-functionalized butenolides that can be further manipulated, thereby rendering them useful synthetic intermediates.",

author = "Masahiro Terada and Kenichi Ando",

year = "2011",

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AU - Ando, Kenichi

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Y1 - 2011/4/15

N2 - The highly syn-diastereo- and enantioselective direct vinylogous Michael addition ofα-thio substituted furanones with conjugate nitroalkenes was demonstrated using an axially chiral guanidine base catalyst. The method provides facile access to enantioenriched α,γ-functionalized butenolides that can be further manipulated, thereby rendering them useful synthetic intermediates.

AB - The highly syn-diastereo- and enantioselective direct vinylogous Michael addition ofα-thio substituted furanones with conjugate nitroalkenes was demonstrated using an axially chiral guanidine base catalyst. The method provides facile access to enantioenriched α,γ-functionalized butenolides that can be further manipulated, thereby rendering them useful synthetic intermediates.

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Enantioselective direct vinylogous michael addition of functionalized furanones to nitroalkenes catalyzed by an axially chiral guanidine base

Abstract

ASJC Scopus subject areas

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