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

60 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

Access to Document

10.1021/ol800745q

Cite this

@article{8b1cd91b0b5549368cd4bd90bf91e0da,

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",

language = "English (US)",

volume = "10",

pages = "2449--2452",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "12",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=48849102178&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=48849102178&partnerID=8YFLogxK

U2 - 10.1021/ol800745q

DO - 10.1021/ol800745q

M3 - Article

C2 - 18476709

AN - SCOPUS:48849102178

SN - 1523-7060

VL - 10

SP - 2449

EP - 2452

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this