Lewis acid-catalyzed conjugate additions of silyloxyallenes: A selective solution to the intermolecular Rauhut-Currier problem

Troy E. Reynolds; Michael S. Binkley; Karl A. Scheidt

doi:10.1021/ol800745q

Lewis acid-catalyzed conjugate additions of silyloxyallenes: A selective solution to the intermolecular Rauhut-Currier problem

Troy E. Reynolds, Michael S. Binkley, Karl A. Scheidt

Chemistry

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

59 Scopus citations

Abstract

(Chemical Equation Presented) Silyloxyallenes serve as highly useful α-acylvinyl anion equivalents. These latent allenolates undergo conjugate additions to alkylidene malonates in the presence of 10 mol % Sc(OTf) ₃. The reaction delivers intermolecular Rauhut-Currier products in excellent yields and regioselectivities for a wide scope of substrates. Notably, the formal cross-coupling of two different α,β-unsaturated carbonyl compounds (a cross Rauhut-Currier reaction) is achieved. Preliminary investigations have demonstrated good levels of enantioselectivity for the addition of a racemic silyloxyallene with a chiral Lewis acid.

Original language	English (US)
Pages (from-to)	2449-2452
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	12
DOIs	https://doi.org/10.1021/ol800745q
State	Published - 2008

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Lewis acid-catalyzed conjugate additions of silyloxyallenes: A selective solution to the intermolecular Rauhut-Currier problem",

abstract = "(Chemical Equation Presented) Silyloxyallenes serve as highly useful α-acylvinyl anion equivalents. These latent allenolates undergo conjugate additions to alkylidene malonates in the presence of 10 mol % Sc(OTf) 3. The reaction delivers intermolecular Rauhut-Currier products in excellent yields and regioselectivities for a wide scope of substrates. Notably, the formal cross-coupling of two different α,β-unsaturated carbonyl compounds (a cross Rauhut-Currier reaction) is achieved. Preliminary investigations have demonstrated good levels of enantioselectivity for the addition of a racemic silyloxyallene with a chiral Lewis acid.",

author = "Reynolds, {Troy E.} and Binkley, {Michael S.} and Scheidt, {Karl A.}",

year = "2008",

doi = "10.1021/ol800745q",

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T1 - Lewis acid-catalyzed conjugate additions of silyloxyallenes

T2 - A selective solution to the intermolecular Rauhut-Currier problem

AU - Reynolds, Troy E.

AU - Binkley, Michael S.

AU - Scheidt, Karl A.

PY - 2008

Y1 - 2008

N2 - (Chemical Equation Presented) Silyloxyallenes serve as highly useful α-acylvinyl anion equivalents. These latent allenolates undergo conjugate additions to alkylidene malonates in the presence of 10 mol % Sc(OTf) 3. The reaction delivers intermolecular Rauhut-Currier products in excellent yields and regioselectivities for a wide scope of substrates. Notably, the formal cross-coupling of two different α,β-unsaturated carbonyl compounds (a cross Rauhut-Currier reaction) is achieved. Preliminary investigations have demonstrated good levels of enantioselectivity for the addition of a racemic silyloxyallene with a chiral Lewis acid.

AB - (Chemical Equation Presented) Silyloxyallenes serve as highly useful α-acylvinyl anion equivalents. These latent allenolates undergo conjugate additions to alkylidene malonates in the presence of 10 mol % Sc(OTf) 3. The reaction delivers intermolecular Rauhut-Currier products in excellent yields and regioselectivities for a wide scope of substrates. Notably, the formal cross-coupling of two different α,β-unsaturated carbonyl compounds (a cross Rauhut-Currier reaction) is achieved. Preliminary investigations have demonstrated good levels of enantioselectivity for the addition of a racemic silyloxyallene with a chiral Lewis acid.

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Lewis acid-catalyzed conjugate additions of silyloxyallenes: A selective solution to the intermolecular Rauhut-Currier problem

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